cas 19790-60-4, 3-BENZYLOXY-PROPIONALDEHYDE

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Chiral polypropionate subunit by a chemoenzymatic approach
Enzymatic desymmetrization of meso-4-methyl-3,5-syn-dioxolan- 1,3,5,7- tetrol was found to be highly enantioselective leading to both acetylated enantiomers with high enantiomeric excess.
Bonini,Chiummiento,Funicello,Marconi,Righi
p. 2559 - 2561
(1998)
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Anionically induced domino reactions; synthesis of analogues of marine sesquiterpenes
An anionically induced domino reaction is the key step in the synthesis of the isotwistane skeleton. This precursor can be transformed into the marine sesquiterpene 2-isocyanopupukeanane or its structural analogues.
Gutke, Hans-Jürgen,Oesterreich, Kai,Spitzner, Dietrich,Braun, Norbert A
p. 997 - 1003
(2001)
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Asymmetric synthesis of D- and L-2-deoxy-4-thioriboses
Both D- and L-enantiomers of 2-deoxy-4-thioribose derivatives 12 and 17 were prepared stereospecifically in 12 steps from 1,3-propanediol. The key intermediary 2,3-epoxy alcohols, 8 and 15 were obtained with high enantiomeric excess by the Sharpless asymmetric epoxidation using (+)-L- diethyl tartrate and (-)-D-diethyl tartrate.
Uenishi,Motoyama,Takahashi
p. 101 - 110
(1994)
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Total stereocontrolled synthesis of a novel pyrrolizidine iminosugar
Herein we describe a versatile approach to the pyrrolizidine alkaloids skeleton by tailoring our original strategy already used for the pyrrolidine iminosugars synthesis. The key steps are the regio- and stereoselective azidolysis of the suitable chiral v
De Angelis, Martina,Primitivo, Ludovica,Lizzio, Federica,Agostinelli, Sonia,Sappino, Carla,Ben Romdan, Ilaria,Bonanni, Luciano,D'Annibale, Andrea,Antonioletti, Roberto,Ricelli, Alessandra,Righi, Giuliana
(2021/12/20)

Pyrazole Agonist of the Apelin Receptor Improves Symptoms of Metabolic Syndrome in Mice
Apelin receptor agonism improves symptoms of metabolic syndrome. However, endogenous apelin peptides have short half-lives, making their utility as potential drugs limited. Previously, we had identified a novel pyrazole-based agonist scaffold. Systematic modification of this scaffold was performed to produce compounds with improved ADME properties. Compound 13 with favorable agonist potency (cAMPi EC50 = 162 nM), human liver microsome stability (T1/2 = 62 min), and pharmacokinetic profile in rodents was identified. The compound was tested in a mouse model of diet-induced obesity (DIO) and metabolic syndrome for efficacy. Treatment with 13 led to significant weight loss, hypophagia, improved glucose utilization, reduced liver steatosis, and improvement of disease-associated biomarkers. In conclusion, a small-molecule agonist of the apelin receptor has been identified that is suitable for in vivo investigation of the apelinergic system in DIO and perhaps other diseases where this receptor has been implicated to play a role.
Narayanan, Sanju,Wang, Shaobin,Vasukuttan, Vineetha,Vyas Devambatla, Ravi Kumar,Dai, Donghua,Jin, Chunyang,Snyder, Rodney,Laudermilk, Lucas,Runyon, Scott P.,Maitra, Rangan
p. 3006 - 3025
(2021/04/06)

GDC-9545 (Giredestrant): A Potent and Orally Bioavailable Selective Estrogen Receptor Antagonist and Degrader with an Exceptional Preclinical Profile for ER+ Breast Cancer
Breast cancer remains a leading cause of cancer death in women, representing a significant unmet medical need. Here, we disclose our discovery efforts culminating in a clinical candidate, 35 (GDC-9545 or giredestrant). 35 is an efficient and potent selective estrogen receptor degrader (SERD) and a full antagonist, which translates into better antiproliferation activity than known SERDs (1, 6, 7, and 9) across multiple cell lines. Fine-tuning the physiochemical properties enabled once daily oral dosing of 35 in preclinical species and humans. 35 exhibits low drug-drug interaction liability and demonstrates excellent in vitro and in vivo safety profiles. At low doses, 35 induces tumor regressions either as a single agent or in combination with a CDK4/6 inhibitor in an ESR1Y537S mutant PDX or a wild-type ERα tumor model. Currently, 35 is being evaluated in Phase III clinical trials.
Liang, Jun,Zbieg, Jason R.,Blake, Robert A.,Chang, Jae H.,Daly, Stephen,Dipasquale, Antonio G.,Friedman, Lori S.,Gelzleichter, Thomas,Gill, Matthew,Giltnane, Jennifer M.,Goodacre, Simon,Guan, Jane,Hartman, Steven J.,Ingalla, Ellen Rei,Kategaya, Lorn,Kiefer, James R.,Kleinheinz, Tracy,Labadie, Sharada S.,Lai, Tommy,Li, Jun,Liao, Jiangpeng,Liu, Zhiguo,Mody, Vidhi,McLean, Neville,Metcalfe, Ciara,Nannini, Michelle A.,Oeh, Jason,O'Rourke, Martin G.,Ortwine, Daniel F.,Ran, Yingqing,Ray, Nicholas C.,Roussel, Fabien,Sambrone, Amy,Sampath, Deepak,Schutt, Leah K.,Vinogradova, Maia,Wai, John,Wang, Tao,Wertz, Ingrid E.,White, Jonathan R.,Yeap, Siew Kuen,Young, Amy,Zhang, Birong,Zheng, Xiaoping,Zhou, Wei,Zhong, Yu,Wang, Xiaojing
supporting information
p. 11841 - 11856
(2021/07/31)

CYCLOALKYL-CONTAINING CARBOXYLIC ACIDS AND USES THEREOF
The present application discloses a compound of formula (I) or a salt thereof: (I) and compositions comprising such compound or salt thereof. The use of such compound, salt thereof or composition comprising same for treating anemia or leukopenia, fibrosis, cancer, hypertension and/or a metabolic condition in a subject is also disclosed.
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Page/Page column 55

(2021/06/26)

Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades
A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.
Wang, Hong-Fa,Guo, Lin-Na,Fan, Zhi-Bo,Tang, Tian-Hua,Zi, Weiwei
p. 2676 - 2681
(2021/04/12)

Synthesis of salicylate and salicylamide alcohols for the preparation of phosphorodiamidates and ifosfamide prodrugs
Prodrugs are derivatives of drugs which gives parent drug or release drug when it breaks inside the body by the presence of suitable enzyme, and then exert desired pharmacological effect. For many years, prodrug strategy has been developed enormously to solve many unwanted drug properties. In drug discovery and development, prodrugs have well-known pharmacokinetic effects of pharmacologically nimble products. Almost 10% of drugs permitted whole world are classified as prodrugs, where the application of a prodrug method during initial stages of development is an emergent fashion. Phosphorodiamidates prodrugs are well known anticancer agents particularly against leucomia. To improve the selectivity of the chemotherapeutic agents and reduce systemic toxicity, I herein report different types of salicylate and salicylamide alcohols for the preparation of phosphorodiamidates and ifosfamide prodrugs.
Pal, Ashutosh
p. 295 - 301
(2021/05/19)

Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds.
Yoo, Jae Won,Seo, Youngran,Park, Jong Beom,Kim, Young Gyu
(2020/01/13)

BET BROMODOMAIN PROTEIN DEGRADERS WITH CLEAVABLE LINKERS
The present disclosure provides compounds represented by Formula (I): Formula (I) and the pharmaceutically acceptable salts and solvates thereof, wherein R1, R2a, R2b, R3a, R3b, R4, Y, =, Ar, W, L, and B are as defined as set forth in the specification. The present disclosure also provides compounds of Formula (I)I for use to treat a condition or disorder responsive to inhibition and/or degradation of BET bromodomains such as cancer.
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Paragraph 0359-0360

(2019/04/11)

Trogoderma granarium sex pheromone and preparation method thereof
The invention discloses trogoderma granarium sex pheromone and a preparation method thereof. The preparation method comprises the following steps: enabling (R)-2-methylbutanol to react with 5-sulfydryl-1-phenyltetrazole Mitsnobu to obtain A; enabling A to react with peroxy acid to obtain B; enabling 1,3-propanediol to react with benzyl chloride under an alkaline condition to obtain C; oxidizing Cto obtain a compound D; enabling B to react with D and hexamethyldisilamine lithium salt to obtain E; catalytically hydrogenating E by virtue of palladium to obtain F; enabling F, iodine, tertiary phosphine and imidazole to obtain G; obtaining H by using 1,8-octylene glycol and benzyl chloride and alkali; oxidizing H to obtain I; obtaining J by using I, carbon tetrabromide and triphenylphosphine Corey-Fush; obtaining K by using J and strong alkali; obtaining L by using K and G and alkali; obtaining M by using L, ethyl mercaptan and boron trifluoride diethyl etherate solution; catalytically hydrogenating M by virtue of metal to obtain N; and oxidizing N to obtain a target product, wherein a chemical name of the target product is (R,Z)-14-methylhexadeca-8-ene-1-aldehyde, thus obtaining the trogoderma granarium sex pheromone. The preparation method disclosed by the invention is low in cost and high in yield.
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Paragraph 0041; 0056; 0062; 0063; 0064; 0065

(2019/02/17)

Selective alkyl ether cleavage by cationic bis(phosphine)iridium complexes
Catalysts capable of heterolytic silane activation have been successfully applied to the conversion of alkyl ethers to silyl ethers via C-O bond cleavage. The previously-reported cationic pincer-supported iridium complex for this transformation suffers fr
Jones, Caleb A. H.,Schley, Nathan D.
supporting information
p. 1744 - 1748
(2019/02/20)

A Catalytic Asymmetric Protecting-Group-Free Total Synthesis of (4 S,5 S)-4,8-Dihydroxy-3,4-dihydrovernoniyne and Its Enantiomer
A catalytic asymmetric second generation synthesis of (4S,5S)-4,8-dihydroxy-3,4-dihydrovernoniyne has been completed employing the asymmetric dihydroxylation strategy. Further, a four-step protecting-group-free synthesis of the natural product and its enantiomer has been achieved through the modified Knoevenagel reaction, asymmetric dihydroxylation, and Cadiot-Chodkiewicz coupling. The protecting-group-free synthesis is completed in four steps and 41% overall yield.
Ramakrishna, Gujjula V.,Fernandes, Rodney A.
p. 14127 - 14132
(2019/10/17)

TYPE II TOPOISOMERASE INHIBITORS AND METHODS OF MAKING AND USING THEREOF
Disclosed are Type II Topoisomerase Inhibitors, analogs thereof, pharmaceutical compositions thereof, and methods of making and using these compounds and compositions. Methods of using the disclosed compounds to treat infections, such as MRSA, MDR P. aeruginosa, and other pathogens are also described.
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Page/Page column 38; 40

(2018/11/22)

Selective Aerobic Oxidation of Alcohols with NO3? Activated Nitroxyl Radical/Manganese Catalyst System
A homogeneous Mn(NO3)2/2,2,6,6-tetramethylpiperidin-1-yl)oxyl/2-picolinic acid catalyst system is highly active and versatile for the selective aerobic oxidation of alcohols (2,2,6,6-tetramethylpiperidin-1-yl)oxyl=TEMPO, 2-picolinic acid=PyCOOH). The catalytic method enables near quantitative conversion of various primary alcohols to the respective aldehydes using a very simple reaction setup and workup. This study presents findings on the catalyst stability and mechanisms of deactivation. The results show that NO3? plays a crucial catalytic role in the reaction as a source of oxygen activating NOx species. Yet, disproportionation of NO3? to the volatile NO2 during the reaction leads to catalyst deactivation under open air conditions. Catalyst deactivation through this route can be overcome by adding a catalytic amount of nitrate salt, for example NaNO3 into the reaction. This stabilizes the Mn(NO3)2/TEMPO/PyCOOH catalyst and enables oxidation of various primary alcohols to the respective aldehydes using low catalyst loadings under ambient conditions. Secondary alcohols can be oxidized with a modified catalyst utilizing sterically accessible nitroxyl radical 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO) instead of TEMPO. At the end of the alcohol oxidation, pure carbonyl products and the reusable catalyst can be recovered simply by extracting with organic solvent and dilute aqueous acid, followed by evaporation of both phases.
Lagerblom, Kalle,Keskiv?li, Juha,Parviainen, Arno,Mannisto, Jere,Repo, Timo
p. 2908 - 2914
(2018/05/03)

Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C-H Alkylation
Radical cyclization represents a powerful strategy for construction of ring structures. Traditional radical cyclization, which is based on radical addition as the key step, necessitates the use of unsaturated substrates. Guided by the concept of metalloradical catalysis, a different mode of radical cyclization that can employ saturated C-H substrates is demonstrated through the development of a Co(II)-based system for catalytic activation of aliphatic diazo compounds for enantioselective radical alkylation of various C(sp3)-H bonds. It allows for efficient construction of chiral pyrrolidines and other valuable 5-membered cyclic compounds. This alternative strategy of radical cyclization provides a new retrosynthetic paradigm to prepare five-membered cyclic molecules from readily available open-chain aldehydes through the union of C-H and C=O elements for C-C bond formation.
Wang, Yong,Wen, Xin,Cui, Xin,Zhang, X. Peter
supporting information
p. 4792 - 4796
(2018/04/17)

Facile Conversion of α-Acyloxy Amides into 3-Hydroxy-lactams
The new synthetic route to α-acyloxy amides based on Passerini multicomponent reaction followed by transformation into the corresponding five-, six-, and seven-membered 3-hydroxy-lactams has been proposed. The influence of the reaction conditions, which includes substrate structure on the reaction course that led to desired lactams, was studied. The use of various oxo components in the Passerini multicomponent reaction (P-MCR) has been evaluated. The first example of a semicyclic O,O-acetal employed as an aldehyde equivalent in the P-MCR has been reported. Finally, the established protocol was successfully applied for the enantioselective synthesis of 3-hydroxy-lactams, which play a crucial role in the synthesis of the number of bioactive compounds.
Koszelewski, Dominik,Trzepizur, Damian,Zaorska, Ewelina,Madej, Arleta,Brodzka, Anna,Paprocki, Daniel,Borys, Filip,Wilk, Monika,Ostaszewski, Ryszard
p. 3280 - 3290
(2018/07/13)

TETRAHYDRO-PYRIDO[3,4-b]INDOLE ESTROGEN RECEPTOR MODULATORS AND USES THEREOF
Described herein are tetrahydro-pyrido[3,4-b]indol-1-yl compounds with estrogen receptor modulation activity or function having the Formula I structure: and stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, and with the substituents and structural features described herein. Also described are pharmaceutical compositions and medicaments that include the Formula I compounds, as well as methods of using such estrogen receptor modulators, alone and in combination with other therapeutic agents, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.
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Paragraph 0365; 0366

(2018/01/18)

MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF
The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 0472; 0473

(2017/05/15)

Practical Aerobic Oxidation of Alcohols: A Ligand-Enhanced 2,2,6,6-Tetramethylpiperidine-1-oxy/Manganese Nitrate Catalyst System
A highly efficient, ligand-enhanced 2,2,6,6-tetramethylpiperidine-1-oxy (TEMPO)/Mn(NO3)2 catalyst system for the aerobic oxidation of alcohols is described. From the series of coordinating ligands studied herein, 2-picolinic acid (PyCOOH) improves the catalytic activity of TEMPO/Mn(NO3)2 remarkably. Under ambient air at room temperature in acetic acid, the ligand-enhanced catalyst converts aliphatic and benzylic primary alcohols that bear various functional groups into their respective aldehydes with near quantitative conversions. The applicability of the catalyst for convenient preparative synthesis was demonstrated by conducting oxidations on a gram scale. A change of TEMPO to the sterically less demanding 9-azabicyclo[3.3.1]nonane N-oxyl results in a Mn catalyst that is also able to oxidize secondary alcohols to ketones. Mechanistic studies showed that alcohols are oxidized by the oxoammonium cation derived from the nitroxyl radical. The active oxidant is regenerated by Mn(NO3)2, and this process is greatly promoted by the coordination of PyCOOH to Mn.
Lagerblom, Kalle,Lagerspets, Emi,Keskiv?li, Juha,Cook, Chris,Ekholm, Filip,Parviainen, Arno,Repo, Timo
p. 3880 - 3887
(2017/09/28)

Visible-light-mediated achmatowicz rearrangement
Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelfstable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4 as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.
Plutschack, Matthew B.,Seeberger, Peter H.,Gilmore, Kerry
supporting information
p. 30 - 33
(2017/11/28)

BIPOLAR TETRAETHER LIPIDS
Disclosed herein, inter alia, are compounds, compositions, and liposomes and methods of thereof.
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Paragraph 0450; 0463; 0464

(2017/03/21)

AMINO PYRAZOLONE DERIVATIVE HAVING CONDENSED RING STRUCTURE
PROBLEM TO BE SOLVED: To provide a compound that has excellent inhibitory action on ATPase activity of TIP48/TIP49 complex and is therefore useful for the treatment of tumor, or a pharmacologically acceptable salt thereof. SOLUTION: The present invention provides a compound having a structure represented by general formula (I), its pharmacologically acceptable salt, or a pharmaceutical composition comprising the compound (where R3, R4, R5, R6, R7, W, X, Y, and Z are as defined in the specifications). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0227; 0228; 0229; 0230

(2016/10/08)

Regioselective dihydropyran formation from 4-iodo-2,6-disubstituted tetrahydropyran derivatives using In(OAc)3/LiI system as the promoter
The rapid and regioselective synthesis of a series of 2,6-disubstituted dihydropyranic building-blocks bearing an oxygenated side chain is described. The corresponding 4-iodo tetrahydropyran precursors, easily prepared by Prins cyclization, underwent regi
Chalopin, Thibaut,Jebali, Khaoula,Gaulon-Nourry, Catherine,Dénès, Fabrice,Lebreton, Jacques,Mathé-Allainmat, Monique
p. 318 - 327
(2015/12/30)

C-20 STEROID COMPOUNDS, COMPOSITIONS AND USES THEREOF TO TREAT TRAUMATIC BRAIN INJURY (TBI), INCLUDING CONCUSSIONS
The present invention relates to C-20 steroid compounds, compositions and methods of use thereof to treat, minimize and/or prevent traumatic brain injury (TBI), including severe TBI, moderate TBI and mild TBI, including concussions.
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(2016/04/09)

C-20 STEROID COMPOUNDS, COMPOSITIONS, AND USES THEREOF TO TREAT TRAUMATIC BRAIN INJURY (TBI), INCLUDING CONCUSSIONS
The present invention relates to C-20 steroid compounds, compositions and methods of use thereof to treat, minimize and/or prevent traumatic brain injury (TBI), including severe TBI, moderate TBI and mild TBI, including concussions.
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(2017/01/09)

Cyclohexane Rings Reduce Membrane Permeability to Small Ions in Archaea-Inspired Tetraether Lipids
Extremophile archaeal organisms overcome problems of membrane permeability by producing lipids with structural elements that putatively improve membrane integrity compared to lipids from other life forms. Herein, we describe a series of lipids that mimic some key structural features of archaeal lipids, such as: 1) single tethering of lipid tails to create fully transmembrane tetraether lipids and 2) the incorporation of small rings into these tethered segments. We found that membranes formed from pure tetraether lipids leaked small ions at a rate that was about two orders of magnitude slower than common bilayer-forming lipids. Incorporation of cyclopentane rings into the tetraether lipids did not affect membrane leakage, whereas a cyclohexane ring reduced leakage by an additional 40 %. These results show that mimicking certain structural features of natural archaeal lipids results in improved membrane integrity, which may help overcome limitations of many current lipid-based technologies.
Koyanagi, Takaoki,Leriche, Geoffray,Onofrei, David,Holland, Gregory P.,Mayer, Michael,Yang, Jerry
supporting information
p. 1890 - 1893
(2016/02/03)

Stable TEMPO and ABNO Catalyst Solutions for User-Friendly (bpy)Cu/Nitroxyl-Catalyzed Aerobic Alcohol Oxidation
Two solutions, one consisting of bpy/TEMPO/NMI and the other bpy/ABNO/NMI (bpy =2,2′-bipyridyl; TEMPO = 2,2,6,6-tetramethylpiperidine N-oxyl, ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl; NMI = N-methylimidazole), in acetonitrile are shown to have good long-term stability (≥1 year) under air at 5 °C. The solutions may be combined in appropriate quantities with commercially available [Cu(MeCN)4]OTf to provide a convenient catalyst system for the aerobic oxidation of primary and secondary alcohols.
Steves, Janelle E.,Stahl, Shannon S.
p. 11184 - 11188
(2015/11/18)

Total Synthesis, Stereochemical Revision, and Biological Reassessment of MandelalideA: Chemical Mimicry of Intrafamily Relationships
MandelalideA and three congeners had recently been isolated as the supposedly highly cytotoxic principles of an ascidian collected off the South African coastline. Since these compounds are hardly available from the natural source, a concise synthesis rou
Willwacher, Jens,Heggen, Berit,Wirtz, Conny,Thiel, Walter,Fürstner, Alois
supporting information
p. 10416 - 10430
(2015/07/07)

Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
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Paragraph 1929

(2015/09/22)

Total Synthesis of (+)-Cryptocaryol A Using a Prins Cyclization/Reductive Cleavage Sequence
The total synthesis of (+)-cryptocaryol A was achieved in 20 steps from (R)-glycidol. The key steps were a Prins cyclization/reductive cleavage sequence to construct the C5-C11 polyol fragment, a diastereoselective aldol reaction to control the stereogeni
Brun, Elodie,Bellosta, Véronique,Cossy, Janine
p. 8668 - 8676
(2015/09/15)

An efficient strategy for the synthesis of syn 1,3-diols via iterative acetate aldol reactions and synthesis of atorvastatin lactone
An efficient strategy for the synthesis of syn 1,3-diol has been developed, employing an imidazolidinone based chiral auxiliary via stereoselective and sequential double acetate aldol reactions. The syn 1,3-diol subunit was modified to obtain the C-7 carboxylic acid side chain and further subjected to reaction with a suitable 1,4-diketone under Paal-Knorr conditions to obtain atorvastatin lactone.
Goyal, Sandeep,Patel, Bhautikkumar,Sharma, Ratnesh,Chouhan, Mangilal,Kumar, Kapil,Gangar, Mukesh,Nair, Vipin A.
supporting information
p. 5409 - 5412
(2015/09/15)

Stereoselective synthesis of two highly potent 5-oxo-ETE receptor antagonists
Enantioselective synthesis of highly potent 5-oxo-ETE receptor antagonists 5a and 6a with a high level of enantiomeric purity is described. The main feature of this work is the simple and efficient synthesis of the bi-functionalized 3-(S)-methyl-pentanedi
Nagendra Reddy, Chintam,Ye, Qiuji,Chourey, Shishir,Gravel, Sylvie,Powell, William S.,Rokach, Joshua
p. 6896 - 6899
(2015/11/27)

HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS AND COMBINATIONS THEREOF
Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds and combinations of such compounds and other therapeutic agents.
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Page/Page column 262; 263

(2015/07/07)

Oxidation of aminoalkyl and hydroxylaminoalkyl furans
The oxidation reactions of amino and hydroxylamino substituted alkylfurans were explored for the synthesis of structurally complex compounds from simple starting materials. A novel photooxygenation of the furan derivatives gave an α,β-unsaturated dicarbonyl moiety which underwent subsequent conjugate addition to yield diastereomeric mixtures of the corresponding pyrrolidine and isoxazoline heterocycles. Oxidation of the α,β-unsaturated dicarbonyl using mCPBA gave epoxide intermediates, which were opened by nucleophilic attack of the amino groups, furnishing pyrrolidine and isoxazolidine heterocycles.
Kazancioglu, Mustafa Zahrittin,Akin Kazancioglu, Elif,Secen, Hasan,Altundas, Ramazan
supporting information
p. 6994 - 6997
(2015/11/27)

Tsuji-Wacker Oxidation of Terminal Olefins using a Palladium-Carbon Nanotube Nanohybrid
Palladium nanoparticles supported on carbon nanotubes were used in the Tsuji-Wacker oxidation. The palladium-based nanohybrid was found to be very active in combination with cuprous chloride for the selective oxidation of terminal olefins into methyl ketones. The co-catalytic system operates under very mild and sustainable conditions (room temperature, atmospheric pressure, low catalyst loading), as opposed to previously reported catalysts, and can be recycled without any loss in activity. Give it a whack: Palladium nanoparticles supported on carbon nanotubes are used in combination with cuprous chloride for the selective Tsuji-Wacker oxidation of terminal olefins into methyl ketones. The co-catalytic system operates under very mild and sustainable conditions and can be recycled without any loss in activity.
Donck, Simon,Gravel, Edmond,Shah, Nimesh,Jawale, Dhanaji V.,Doris, Eric,Namboothiri, Irishi N. N.
p. 2318 - 2322
(2015/08/11)

Oxidative asymmetric umpolung alkylation of Evans' β-ketoimides using dialkylzinc nucleophiles
Umpolung alkylation of Evans' auxiliary substituted β-ketoimides affords the diastereomerically pure products in yields ranging from 40 to 80%. The reaction itself proceeds with diastereoselectivities between 3:1 and 18:1. Dialkylzinc serves as the nucleo
Targel, Tom A.,Kumar, Jayprakash N.,Shneider, O. Svetlana,Bar, Sukanta,Fridman, Natalia,Maximenko, Shimon,Szpilman, Alex M.
supporting information
p. 2546 - 2549
(2015/04/14)

SYNTHESIS OF ENT-PROGESTERONE AND INTERMEDIATES THEREOF
The present invention relates to the synthesis of ent-progesterone and intermediates thereof.
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(2015/07/02)

Catalysis-based total synthesis of putative mandelalide A
A concise synthesis of the putative structure assigned to the highly cytotoxic marine macrolide mandelalide A (1) is disclosed. Specifically, an iridium-catalyzed two-directional Krische allylation and a cobalt-catalyzed carbonylative epoxide opening served as convenient entry points for the preparation of the major building blocks. The final stages feature the first implementation of terminal-acetylene metathesis into natural product synthesis, which is remarkable as this class of substrates was beyond reach until very recently; key to success was the use of the highly selective molybdenum alkylidyne complex 42 as the catalyst. Although the constitution and stereochemistry of the synthetic samples are unambiguous, the spectra of 1 as well as of 11-epi-1 deviate from those of the natural product, which implies a subtle but deep-seated error in the original structure assignment. Bitter and sweet: The synthesis of the proposed structure of the cytotoxic macrolide mandelalide A reiterates the notion that structure elucidation of architecturally complex natural products is not always reliable. From the chemical viewpoint, the chosen route attests to the power of (transition) metals as catalysts for stereoselective synthesis. Most notable is the first application of terminal-acetylene metathesis to natural product chemistry.
Willwacher, Jens,Fuerstner, Alois
supporting information
p. 4217 - 4221
(2014/05/06)

A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir
An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.
Peifer, Manuel,Berger, Rapha?lle,Shurtleff, Valerie W.,Conrad, Jay C.,Macmillan, David W. C.
supporting information
p. 5900 - 5903
(2014/05/20)

Synthesis of four diastereomers and structural revision of tetradenolide
Four diastereomers of tetradenolide, a cytotoxic α-pyrone isolated from Tetradenia riparia, were synthesized stereoselectively using the Z-selective Horner-Emmons reaction followed by acid catalyzed lactonization. Making comparison of the 1H an
Tokuda, Maki,Kurogome, Yuji,Katoh, Rieko,Nohara, Yukie,Hattori, Yasunao,Makabe, Hidefumi
p. 4189 - 4192
(2014/07/22)

Simple stereoselective synthesis of unsaturated lactone intermediates and their conversion into natural dihydropyranones and their enantiomers#
The stereoselective synthesis of the unsaturated lactone intermediates, (S) - and (R)-2-(6-oxo-3, 6-dihydro-2Hpyran-2-yl) acetaldehydes has been accomplished from propane 1,3 diol employing Maruoka asymmetric allylation and ring closing metathesis reaction. The intermediates were converted into two natural dihydropyranones, 6 (R)-4-oxopent-2-enyl 5,6-dihydro-2H-pyran-2-one and (R)- rugulactone and their enantiomers through Wittig olefination.
Shinde, Digambar Balaji,Kanth, Boddu Shashi,Satyakumar, Avula,Kamble,Das, Biswanath
p. 317 - 323
(2013/07/26)

Total synthesis and full histone deacetylase inhibitory profiling of azumamides A-E as Well as β2- epi -Azumamide e and β3- epi -Azumamide e
Cyclic tetrapeptide and depsipeptide natural products have proven useful as biological probes and drug candidates due to their potent activities as histone deacetylase (HDAC) inhibitors. Here, we present the syntheses of a class of cyclic tetrapeptide HDAC inhibitors, the azumamides, by a concise route in which the key step in preparation of the noncanonical disubstituted β-amino acid building block was an Ellman-type Mannich reaction. By tweaking the reaction conditions during this transformation, we gained access to the natural products as well as two epimeric homologues. Thus, the first total syntheses of azumamides B-D corroborated the originally assigned structures, and the synthetic efforts enabled the first full profiling of HDAC inhibitory properties of the entire selection of azumamides A-E. This revealed unexpected differences in the relative potencies within the class and showed that azumamides C and E are both potent inhibitors of HDAC10 and HDAC11.
Villadsen, Jesper S.,Stephansen, Helle M.,Maolanon, Alex R.,Harris, Pernille,Olsen, Christian A.
supporting information
p. 6512 - 6520
(2013/09/23)

Enantioselective synthesis of the natural product (S)-rugulactone
A simple and efficient enantioselective synthesis of (6S)-5,6-dihydro-6- [(2E)-4-oxo-6-phenylhex-2-en-1-yl]-2H-pyran-2-one (=(S)-rugulactone) has been accomplished. The synthesis started from commercially available propane-1,3-diol and ethyl 3-phenylpropa
Nagaiah, Burea,Narsaiah, Akkirala Venkat
p. 1948 - 1954
(2013/11/06)

Synthetic studies toward potent cytostatic macrolide bryostatin: An expedient synthesis of C1-C10 fragment
The stereoselective synthesis of C1-C10 fragment of cytostatic macrolide bryostatin is described. Two of the three chiral centers have been established via the Sharpless kinetic resolution of racemic allylic alcohol 15 followed by regioselective reduction
Yadav, J. S.,Aravind, S.,Kumar, G. Mahesh,Reddy, B. V. Subba
p. 6163 - 6166,4
(2012/12/11)

Synthetic studies toward potent cytostatic macrolide bryostatin: An expedient synthesis of C1-C10 fragment
The stereoselective synthesis of C1-C10 fragment of cytostatic macrolide bryostatin is described. Two of the three chiral centers have been established via the Sharpless kinetic resolution of racemic allylic alcohol 15 followed by regioselective reduction
Yadav,Aravind,Kumar, G. Mahesh,Reddy, B.V.Subba
p. 6163 - 6166
(2013/01/14)

Investigation on the chemoenzymatic synthesis of threo- and erythro-β-hydroxy-L-glutamic acid derivatives
A derivative of the malonic semialdehyde was transformed by means of a bioconversion catalyzed by the enzyme L-threonine aldolase from E. coli into a 6:4 epimeric mixture of two precursors of β-hydroxy glutamic acid. The enzyme was selective for the formation of the (S)-configuration at C-2, whereas the configuration at C-3 was not controlled. The two epimers were separated exploiting a diastereoselective acylation in organic solvent catalyzed by lipase PS. The relative and absolute configurations of the products were preliminarily assigned on the base of the model proposed by Kazslauskas for the stereopreference of lipase PS and by comparison of the chemical shifts of the H-2 and H-3 protons of the two homologues. The possibility of transforming the obtained products into β-hydroxy glutamic acid derivatives by conventional chemical reactions was demonstrated.
Sagui, Francesca,De Micheli, Carlo,Roda, Gabriella,Magrone, Pietro,Pizzoli, Rachele,Riva, Sergio
experimental part
p. 27 - 34
(2012/04/10)

Concise total synthesis of dihydrocorynanthenol, protoemetinol, protoemetine, 3-epi-protoemetinol and emetine
A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences. Copyright
Lin, Shuangzheng,Deiana, Luca,Tseggai, Abrehet,Cordova, Armando
p. 398 - 408
(2012/02/16)

Diastereo- and enantioselective iridium-catalyzed carbonyl propargylation from the alcohol or aldehyde oxidation level: 1,3-enynes as allenylmetal equivalents
Axial to axial to point chirality transfer: Exposure of conjugated enynes to alcohols in the presence of an iridium catalyst modified by a segphos ligand results in the generation of aldehyde-allenyliridium pairs and formation of enantiomerically enriched products of carbonyl anti-(α-methyl) propargylation (see scheme). An identical set of products are obtained from aldehydes under related transfer hydrogenation conditions by employing formic acid as a reductant. Copyright
Geary, Laina M.,Woo, Sang Kook,Leung, Joyce C.,Krische, Michael J.
p. 2972 - 2976
(2012/04/18)

The first stereoselective total synthesis of (Z)-cryptomoscatone D2, a natural G2 checkpoint inhibitor
The first stereoselective synthesis of (Z)-cryptomoscatone D2, a naturally occurring G2 checkpoint inhibitor, was accomplished using propane-1,3-diol as the starting material. The Maruoka asymmetric allylation, ring closing metathesis and the h
Reddy, Gandolla Chinna,Balasubramanyam, Penagaluri,Salvanna,Reddy, Thummala Sreenivasulu,Das, Biswanath
p. 2415 - 2417
(2012/05/05)

Ruthenium-catalyzed reductive coupling of 1,3-enynes and aldehydes by transfer hydrogenation: Anti-diastereoselective carbonyl propargylation
Under the conditions of ruthenium-catalyzed transfer hydrogenation employing isopropanol as a source of hydrogen, isopropoxy-substituted enyne 1 b and aldehydes 3 a-3 l engage in reductive coupling to provide products of propargylation 4 a-4 l with good to complete levels of anti- diastereoselectivity. The unprotected tertiary hydroxy moiety of isopropoxy enyne 1 b is required to enforce diastereoselectivity. Deuterium-labeling studies corroborate reversible enyne hydrometalation in advance of carbonyl addition. As demonstrated in the conversion of 4 f-h and 4 k to 5 f-h and 5 k, the isopropoxy group of the product is readily cleaved upon exposure to aqueous sodium hydroxide to reveal the terminal alkyne. Unprotected coupling is better! Ruthenium-catalyzed transfer hydrogenation of enynes in the presence of aldehydes promotes reductive C-C coupling to provide products of propargylation with good to complete levels of anti-diastereoselectivity (see scheme). The unprotected hydroxy group of the isopropoxy-substituted enyne is required to enforce high levels of anti-diastereoselectivity. Copyright
Geary, Laina M.,Leung, Joyce C.,Krische, Michael J.
p. 16823 - 16827
(2013/03/28)

Lewis acid-promoted addition of 1,3-bis(silyl)propenes to aldehydes: A route to 1,3-dienes
The Lewis acid-promoted addition of 1,3-bis(silyl)-propenes to aldehydes to provide the corresponding (E)-1,3-dienes in excellent stereoselectivity and good to excellent yields is reported. The procedure is mild, base-free, and operationally straightforward.
Borg, Tessie,Tuzina, Pavel,Somfai, Peter
experimental part
p. 8070 - 8075
(2011/11/28)