- Identification of N,N-arylalkyl-picolinamide derivatives targeting the RNA-binding protein HuR, by combining biophysical fragment-screening and molecular hybridization
-
Hu proteins are members of the RNA-binding protein (RBP) family and play a pivotal role in the regulation of post-transcriptional processes. Through interaction with selected mRNAs, RBPs regulate their function and stability; as a consequence, RBP dysregu
- Della Volpe,Linciano,Listro,Tumminelli,Amadio,Bonomo,Elgaher,Adam,Hirsch,Boeckler,Vasile,Rossi,Collina
-
-
- Desulfonylative Electrocarboxylation with Carbon Dioxide
-
Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.
- Zhong, Jun-Song,Yang, Zi-Xin,Ding, Cheng-Lin,Huang, Ya-Feng,Zhao, Yi,Yan, Hong,Ye, Ke-Yin
-
supporting information
p. 16162 - 16170
(2021/09/02)
-
- Stereoselective Total Synthesis of (-)-(2 S,4 R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction
-
The first stereoselective total synthesis of (-)-(2S,4R)-3′-methoxy citreochlorol and (-)-(2S,4S)-3′-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group.
- Sunnapu, Ranganayakulu,Banoth, Saikumar Naik,Reyno,Thomas, Aleena,Venugopal, Navyasree,Rajendar, Goreti
-
p. 4103 - 4113
(2020/03/05)
-
- Convenient syntheses of 3-aryl-3,4-dihydroisocoumarins
-
A convenient method for the synthesis of naturally occurring 3,4-dihydroisocoumarins by judicious use of Friedel-Craft acylation, regioselective formylation and oxidative cyclisation reactions is described. O-methylated analogues of montroumarin and thunb
- Limaye, Rohan A.,Joseph, Augustine R.,Natu, Arun D.,Paradkar, Madhusudan V.
-
p. 191 - 194
(2015/06/02)
-
- Simple access to 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones via domino acylative electrocyclization: The first three step total synthesis of the dihydronaphthopyran-4-one class of natural products
-
Intermolecular domino C-acylation/6π-oxaelectrocyclization between β-ketoesters and α,β-unsaturated acid chlorides took place readily in the presence of CaCl2 to afford a variety of polysubstituted 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones, in good yields. The products were successfully exploited as precursors, for a simple and efficient construction of a naphthalene fused pyran-4-one ring system. This intramolecular Friedel-Crafts acylative aromatization approach was useful for the synthesis of the phytogrowth inhibiting dihydronaphthopyranone class of natural products.
- Ilangovan, Andivelu,Sakthivel, Palaniappan
-
p. 55150 - 55161
(2015/01/16)
-
- Controlled-deactivation cannabinergic ligands
-
We report an approach for obtaining novel cannabinoid analogues with controllable deactivation and improved druggability. Our design involves the incorporation of a metabolically labile ester group at the 2′-position on a series of (-)-Δ8-THC a
- Sharma, Rishi,Nikas, Spyros P.,Paronis, Carol A.,Wood, Jodianne T.,Halikhedkar, Aneetha,Guo, Jason Jianxin,Thakur, Ganesh A.,Kulkarni, Shashank,Benchama, Othman,Raghav, Jimit Girish,Gifford, Roger S.,J?rbe, Torbj?rn U. C.,Bergman, Jack,Makriyannis, Alexandros
-
p. 10142 - 10157
(2014/01/17)
-
- KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME
-
The present teachings provide a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. Also described are a pharmaceutical composition and method of use thereof.
- -
-
Page/Page column 78
(2011/10/31)
-
- Controlled anion migrations with a mixed metal Li/K-TMP amide: General application to benzylic metalations
-
A general method is described for benzylic metalation of o-, m-, and p-substituted toluenes using a mixed metal amide base generated from BuLi/KOtBu/TMP at -78 °C in THF. The excellent selectivity achieved can be rationalized by the ability of the mixed metal amide base to facilitate an anion migration from the kinetic (o-aryl) to the benzylic metalation site. Remarkably, this controlled anion migration is achievable with catalytic amounts of TMP at -78 °C.
- Fleming, Patricia,Oshea, Donal F.
-
supporting information; experimental part
p. 1698 - 1701
(2011/04/17)
-
- Efficient synthesis of natural polyphenolic stilbenes: Resveratrol, piceatannol and oxyresveratrol
-
The practical synthesis of important natural polyphenolic stilbenes, including resveratrol, piceatannol and oxyresveratrol, through Perkin methodology is described. Starting from 3,5-dihydoxyacetophenone (1), the common intermediate 3,5-dimethoxyphenylacetic acid (3) can be obtained via methylation and Willgerodt-Kindler reaction. Perkin condensations between (3) and substituted phenylaldehydes 4 furnished E-2,3-diarylacrylic acids 5, followed by decarboxylation in Cu/quinoline giving stilbene intermediates 6 which bear the Z-configuration. Finally, through a simultaneous demethylation/isomerization process in AlI3/CH3CN system, the target compounds 7a-c can be obtained respectively in good to high overall yields. The synthetic method proved to be more concise, trans-specific, mild, economical and commonly applicable.
- Sun, Hong-Yi,Xiao, Chun-Fen,Cai, Yu-Chen,Chen, Yu,Wei, Wen,Liu, Xian-Ke,Lv, Ze-Liang,Zou, Yong
-
experimental part
p. 1492 - 1496
(2010/12/25)
-
- Total synthesis of Cytosporone B
-
The total synthesis of Cytosporone B, a naturally occurring agonist for Nur77, has been accomplished. The key steps are the sequential Grignard reaction and Lemieux-van Rudloff oxidation followed by a deprotection of the methyl aromatic ether to phenol an
- Huang, He,Zhang, Lei,Zhang, Xiaodong,Ji, Xun,Ding, Xiao,Shen, Xu,Jiang, Hualiang,Liu, Hong
-
scheme or table
p. 1041 - 1043
(2010/10/19)
-
- Asymmetric total synthesis of nigerone and ent-nigerone: Enantioselective oxidative biaryl coupling of highly hindered naphthols
-
An enantioselective synthesis of the chiral bisnaphthopyrone natural product nigerone and its enantiomer, ent-nigerone, has been realized. The use of constrained 2-naphthol substrates was critical to producing highly functionalized chiral 1,1′-binaphthols via asymmetric oxidative biaryl coupling with 1,5-diaza-cis-decalin copper complexes. The final natural product was formed via a key eight-step isomerization process of the coupling product, bisisonigerone, and proceeded with retention of the biaryl con iguration. The axial configurations of bisisonigerone and nigerone were definitively established by a combination of circular dichroism (CD) measurements and quantum chemical CD calculations.
- Kozlowski, Marisa C.,Dugan, Elizabeth C.,DiVirgilio, Evan S.,Maksimenka, Katja,Bringmann, Gerhard
-
p. 583 - 594
(2008/02/08)
-
- The first asymmetric total syntheses and determination of absolute configurations of xestodecalactones B and C
-
The first efficient asymmetric total syntheses of xestodecalactones B and C have been accomplished in 10 steps with an overall yield of 22 and 20.2%, respectively. The key steps involve the utility of Evans oxazolidinone-mediated syn-aldol condensations to establish the C-9 configuration and the macrolide ring formation by intramolecular acylation. The absolute configurations of xestodecalactones B and C have been determined via these syntheses.
- Liang, Qiren,Zhang, Jiyong,Quan, Weiguo,Sun, Yongquan,She, Xuegong,Pan, Xinfu
-
p. 2694 - 2697
(2007/10/03)
-
- Mutasynthesis of Glycopeptide Antibiotics: Variations of Vancomycin's AB-Ring Amino Acid 3,5-Dihydroxyphenylglycine
-
In the mutasynthetic approach, the ΔdpgA mutant of the vancomycin-type glycopeptide antibiotic producer Amycolatopsis balhimycina, which is deficient in the synthesis of 3,5-dihydroxyphenylglycine (DPg), was supplemented with synthetic DPg analogues to obtain the corresponding modified glycopeptides. Sterically more demanding 3,5-disubstituted methoxy derivatives as well as monosubstituted DPg analogues were accepted as substrates. These facts indicate that steric and electronic requirements suffice in several cases for the oxidative closure of the AB ring, thus leading to the generation of novel antibiotically active glycopeptide derivatives. The results represent a further step in evaluating the potential of mutasynthesis for peptidic secondary metabolites. Copyright
- Weist, Stefan,Kittel, Claudia,Bischoff, Daniel,Bister, Bojan,Pfeifer, Volker,Nicholson, Graeme J.,Wohlleben, Wolfgang,Suessmuth, Roderich D.
-
p. 5942 - 5943
(2007/10/03)
-
- An efficient synthesis of 3,5-dimethoxyhomophthalic acid, a key intermediate for synthesis of natural isocoumarins
-
3,5-Dimethoxyhomophthalic acid was prepared efficiently in three steps, from 3,5-dimethoxybenzyl bromide via rhodium-catalyzed direct carbonylation to 3,5-dimethoxyphenylacetic acid followed by successive o-formylation and oxidation. Isocoumarins related
- Saeed, Aamer,Rama, Nasim H.,Arfan
-
p. 519 - 522
(2007/10/03)
-
- Synthetic Approach to Hypoxyxylerone, Novel Inhibitor of Topoisomerase I
-
(Equation Presented) A potential route to the topoisomerase I inhibitor hypoxyxylerone is demonstrated by a highly convergent synthesis of the penta(O-methyl) derivative. The key step in the approach is an anionic homo-Fries rearrangement, little used to
- Piettre, Arnaud,Chevenier, Emmanuel,Massardier, Christine,Gimbert, Yves,Greene, Andrew E.
-
p. 3139 - 3142
(2007/10/03)
-
- (Phenylalkylaminoalkyloxy)-heteroaryl-compounds, processes and intermediates for their production and pharmaceutical compositions containing them
-
3-(Phenylalkylaminoalkylozy)-heteroaryl compounds having heart rate lowering and/or anti-ischemic effects, methods for their preparation and pharmaceutical compositions containing them are described. The compounds correspond to the general formula I STR1 or to the general formula XXXI STR2 in which the substituents have the meanings given the specification.
- -
-
-
- Cereal grain resorcinolic lipids: mono and dienoic homologues are present in rye grains
-
Analyses (UV, IR, 1H-NMR, MS) of the main phenolic fraction isolated by sequential separation on normal-phase and argentation chromatography on silica gel confirmed the presence of monoenoic and dienoic homologues of 1,3-dihydroxy-5-n-alkylbenzene in acet
- Kozubek, Arkadiusz,Tyman, John H. P.
-
-
- A Total Synthesis of the Sesquiterpene Quinone Metachromin-A
-
The first total synthesis of the marine natural product metachromin A was accomplished through a convergent synthesis amenable to the preparation of synthetic analogues.The main features of this synthesis are the introduction the oxygenation at C17 employing a Thiele acetoxylation reaction and a stereoselective Horner-Wadsworth-Emmons coupling of a nonstabilized phosphonate with a methyl ketone derivative to generate the required (E)-trisubstituted double bond.
- Almeida, Wanda P.,Correia, Carlos Roque D.
-
p. 1367 - 1370
(2007/10/02)
-
- Combretastatin Analogs via Hydration of Stilbene Derivatives
-
Hydration of the double bond of some stilbene congeners of Picea abies bark by TiCl4.NaBH4 reagent is described.Five racemic 1,2-diphenylethanol derivatives (9-13), structurally related to (R)-(-)combretastatin , have been obtained and characterize
- Mannila, Erkki,Talvitie, Antti
-
p. 1037 - 1040
(2007/10/02)
-
- Synthesis of 3,5-dihydroxyphenylglycine derivatives and the C-terminal dipeptide of vancomycin
-
Syntheses of optically active 3,5-DMPG and racemic 3,5-DHPG, the latter suitably protected for incorporation into linear peptides modelled on vancomycin, are described and a synthesis of the optically pure protected C-terminal dipeptide of vancomycin is p
- Stone, Martin J.,Maplestone, Rachael A.,Man, Shirley K. Rah,Williams, Dudney H.
-
p. 2663 - 2666
(2007/10/02)
-
- ACTIVATED CARBOXYLATES FROM THE PHOTOOXYGENATION OF OXAZOLES; APPLICATION TO THE SYNTHESIS OF RECIFEIOLIDE, CURVULARIN AND MACROLIDES
-
Oxazoles may be used as masked forms of activated carboxylic acids since they readily form triamides on reaction with singlet oxygen.With 2-alkyl-4,5-diphenyloxazoles, the triamides formed on photooxygenation undergo selective nucleophilic attack at the acyl carbonyl derived from the 2-oxazole position.Using 2-(ο-hydroxyalkyl)-4,5-diphenyloxazoles as subsrates, the oxidation-acylation sequence may be employed for the synthesis of macrolides including (+/-)-recifeiolide and (+/-)-di-O-methylcurvularin.
- Wasserman, Harry H.,Gambale, Ronald J.,Pulwer, Mitchell J.
-
p. 4059 - 4067
(2007/10/02)
-
- OXAZOLES AS MASKED ACTIVATED CARBOXYLATES. SYNTHESIS OF (+/-)-DI-O-METHYLCURVULARIN
-
The dimethyl ether of the mold metabolite, curvularin, was synthesized by intramolecular esterification of an activated carboxylate derived from the photooxidation of an oxazole precursor.
- Wasserman, H. H.,Gambale, R. J.
-
p. 4849 - 4852
(2007/10/02)
-