- Efficient and chemoselective hydrogenation of aldehydes catalyzed by well-defined PN3-pincer manganese(ii) catalyst precursors: An application in furfural conversion
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Well-defined and air-stable PN3-pincer manganese(ii) complexes were synthesized and used for the hydrogenation of aldehydes into alcohols under mild conditions using MeOH as a solvent. This protocol is applicable for a wide range of aldehydes containing various functional groups. Importantly, α,β-unsaturated aldehydes, including ynals, are hydrogenated with the CC double bond/CC triple bond intact. Our methodology was demonstrated for the conversion of biomass derived feedstocks such as furfural and 5-formylfurfural to furfuryl alcohol and 5-(hydroxymethyl)furfuryl alcohol respectively.
- Gholap, Sandeep Suryabhan,Dakhil, Abdullah Al,Chakraborty, Priyanka,Li, Huaifeng,Dutta, Indranil,Das, Pradip K.,Huang, Kuo-Wei
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supporting information
p. 11815 - 11818
(2021/11/30)
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- Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis
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Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
- Chen, Violet Yijang,Kwon, Ohyun
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supporting information
p. 8874 - 8881
(2021/03/17)
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- Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds
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A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.
- Yang, Chun-Hua,Fan, Huihui,Li, Huimin,Hou, Shenyin,Sun, Xiangkun,Luo, Donghao,Zhang, Yinchao,Yang, Zhantao,Chang, Junbiao
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supporting information
p. 9438 - 9441
(2019/11/20)
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- Impaired energy processing disorders and mitochondrial deficiency
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Some aspects of the invention provide for a method of treating Impaired Energy Processing Disorders and Mitochondrial Deficiencies using polyunsaturated fatty acids which are modified in certain positions to attenuate oxidative damage by Reactive Oxygen Species (ROS) and/or suppress the rate of formation of reactive products and toxic compounds.
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Page/Page column 44
(2018/09/14)
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- A tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - triene synthetic method of eighteen carbon (by machine translation)
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The invention relates to a natural [...] pheromone component novel synthesis method, in particular relates to a tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene synthetic method, it has [...], is non-toxic and harmless, which belongs to the field of drug synthesis. The invention uses inexpensive and easily obtained a halopropynyl alcohol as the reaction of the starting material, in order to iodo reagent catalytic coupling reaction as a key step, after six-step reaction, smooth synthetic tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene, the operation is simple, low cost, easily obtained and cheap materials, mild reaction conditions, high yield, the large scale preparation. (by machine translation)
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-
Paragraph 0030; 0032
(2018/09/28)
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- Highly enantioselective nickel-catalyzed intramolecular reductive cyclization of alkynones
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The first asymmetric nickel-catalyzed intramolecular reductive cyclization of alkynones is reported. A P-chiral monophosphine and triethylsilane were used as the ligand and the reducing reagent, respectively, to form a series of tertiary allylic alcohols bearing furan/pyran rings in excellent yields and enantioselectivities. This reaction has a broad substrate scope and enabled the efficient synthesis of dehydroxycubebin and chiral dibenzocyclooctadiene skeletons.
- Fu, Wenzhen,Nie, Ming,Wang, Aizhen,Cao, Ziping,Tang, Wenjun
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supporting information
p. 2520 - 2524
(2015/03/04)
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- METHOD FOR THE SYNTHESIS OF DHA
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A method for preparing docosahexaenoic acid (DHA). The method comprises coupling a compound represented by Formula I with a compound represented by Formula II followed by partial hydrogenation to obtain a compound represented by Formula III. The compound represented by Formula III acts as a DHA precursor and thus can be hydrolysed to obtain DHA. Novel starting materials represented by Formula I and Formula II, and synthetic routes for preparing the same are also provided.
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Page/Page column 39-41
(2012/10/08)
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- PROCESS FOR THE MANUFACTURE OF 2-PENTYN-1-OL
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The present invention is directed to a process for the manufacture of 2-pentyn-1-ol starting from 2-propyn-1-ol via the following intermediates (I), (II) wherein R1 is H or linear C1-6 alkyl, R2 is linear C1-6 alkyl or branched C3-6 alkyl and R3 is linear C1-6 alkyl, as well as to the intermediates themselves.
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Page/Page column 8-9
(2012/08/08)
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- ALLEVIATING OXIDATIVE STRESS DISORDERS WITH PUFA DERIVATIVES
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Some aspects of the invention provide for essential fatty acids which are substituted in specific positions to slow down oxidative damage by Reactive Oxygen Species (ROS), and to suppress the rate of consequent formation of reactive products, for the purpose of preventing or reducing the damage associated with oxidative stress associated diseases such as neurological diseases and age-related macular degeneration (AMD).
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Page/Page column 19
(2011/05/08)
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- Stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development
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An efficient stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development, is described. Highlights of the strategy include the utilization of Sharpless asymmetric epoxidation, Yamaguchi lactonization and an olefin cross-metathesis as the key steps.
- Yadav,Somaiah,Ravindar,Chandraiah
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p. 2848 - 2850
(2008/09/20)
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- Synthesis of epothilones, intermediates thereto and analogues thereof
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The present invention provides compounds of formula (I): as described generally and in classes and subclasses herein. The present invention additionally provides pharmaceutical compositions comprising compounds of formula (I) and provides methods of treating cancer comprising administering a compound of formula (I).
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- Efficient control of the diastereoselectivity and regioselectivity in the singlet-oxygen ene reaction of chiral oxazolidine-substituted alkenes by a remote urea NH functionality: Comparison with dimethyldioxirane and m-chloroperbenzoic acid epoxidations
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The singlet-oxygen ene reaction and the epoxidation by DMD of chiral oxazolidine-substituted alkenes, equipped with a free urea NH functionality and a conformationally fixed double bond, proceed in high like diastereoselectivity (up to > 95:5); also a high regioselectivity was found for the 1O2 ene reaction. Capping of the free NH functionality by methylation erases this like selectivity for both oxidants and significantly reduces the regioselectivity in the ene reaction. These data demonstrate effective hydrogen bonding between the remote urea NH functionality and the oxidant that favors the like attack on the C-C double bond. For 1O2, the hydrogen bonding in the exciplex results in preferred hydrogen abstraction from the alkyl group cis to the directing urea functionality.
- Adam,Peters,Peters,Schambony
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p. 7228 - 7232
(2007/10/03)
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- Tetradecatrienyl and tetradecadienyl acetates and their use as sex attractants for tomato pests
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The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.
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- Synthesis of stegobiol and its oxidation to stegobinone, the components of the female-produced sex pheromone of the drugstore beetle
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Crystalline (-)-stegobinone [(2S,3R,1′R)]-2,3-dihydro-2,3,5-trimethyl-6-(1′-methyl-2′- oxobutyl)-4H-pyran-4-one (1)], the major component of the female-produced sex pheromone of the drugstore beetle (Stegobium paniceum L.), was synthesized by oxidation of crystalline and the minor component (-)-stegobiol [(2S,3R,1′S,2′S)-2,3-dihydro-2,3,5-trimethyl-6-(2′-hydroxy- 1′-methylbutyl)-4H-pyran-4-one (2)] under the appropriate conditions using Jones's chromic acid, Dess-Martin's periodinane or Ley's ruthenium reagent. The latter (2) was synthesized by employing lipase and the Sharpless epoxidation for the introduction of the proper chiral centers. The streostructure of 1 was comfirmed by X-ray analysis.
- Mori, Kenji,Sano, Satoshi,Yokoyama, Yusuke,Bando, Masahiko,Kido, Masaru
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p. 1135 - 1141
(2007/10/03)
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- (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, major sex pheromone component of the tomato pest Scrobipalpuloides absoluta (Lepidoptera: Gelechiidae)
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The major sex attractant emitted by Scrobipalpuloides absoluta females is shown to be (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate by a novel strategy involving the random reduction of double bonds, followed by methylthiolation of the reduced products. Each female sex gland contains ca. 1-5 ng of this pheromone. This triene ester, synthesized by a stereospecific procedure, shows spectral and gas chromatographic properties identical to those of the natural substance. In field tests and wind tunnel bioassays, the synthetic ester was found to be highly attractive to conspecific males. The male response to this pheromone, however, is restricted to the same early-morning time window during which females exhibit calling behavior.
- Attygalle, Athula B.,Jham, Gulab N.,Svatos, Ales,Frighetto, Rosa T. S.,Ferrara, Fernando A.,Vilela, Evaldo F.,Uchoa-Fernandes, Manoel A.,Meinwald, Jerrold
-
p. 305 - 314
(2007/10/03)
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- Synthesis of Deuterium Labeled Polyunsaturated Fatty Acids
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Compounds containing carbon-carbon double bonds bearing cis deuterium atoms can be prepared conveniently by treating disubstituted acetylenes with bis(2-deuteriocyclohexyl)borane-B-D1 followed by reaction with CH3CO2D.As an example, the preparation of labeled linolenic acid is reported.
- Svatos, Ales,Attygalle, Athula B.,Meinwald, Jerrold
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p. 9497 - 9500
(2007/10/02)
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- COMPOUNDS WITH HERBAL ODOR. V. UNBRANCHED PRIMARY (Z)-ALKENOLS
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The similarity between the odor of alkenols (Z)-CH3-(CH2)n(H=CH(CH2)mOH and the odor of leaf alcohol (m=2, n=1), taken as standard, gradually weakened with change in the m and/or n values and is determined by the number of carbon atoms in the molecules.
- Vasil'ev, A. A.,Cherkaev, G. V.,Nikitina, M. A.
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p. 735 - 739
(2007/10/02)
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- ISOLATION AND TOTAL SYNTHESIS OF THE MAJOR CONSTITUENT OF THE ROOTS OF CENTAUREA INCANA: APLOTAXENE
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The major constituent of the petroleum ether extract of the root of Centaurea incana was identified as (8Z,11Z,14Z)-1,8,11,14-heptadecatetraene (Aplotaxene 1).A convergent and highly stereoselective synthesis of this compound is reported.
- Cossy, J.,Aclinou, P.
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p. 7615 - 7618
(2007/10/02)
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- 2,5,6,7-tetranor-18,18,19,19-tetradehydro-4,8-inter-m-phenylene PGI2 derivatives
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Disclosed herein are novel prostaglandin I2 (PGI2) derivatives exhibiting excellent physiological activities, said derivatives being represented by the general formula: STR1 wherein R1, R2 and R3 are as defined herein.
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- STEREOSELECTIVE SYNTHESIS OF (9Z,15Z)-(11S,12S,13S)-11-HYDROXY-12,13-EPOXY OCTADECADIENOIC ACID: A CONSTITUENT OF RICE PLANT INFECTED WITH RICE BLAST DISEASE
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An elegant, stereoselective synthesis of (9Z,15Z)-(11S,12S,13S)-11-hydroxy-12,13-epoxy octadecadienoic acid (1) by enantioselective epoxidation is described.
- Rama Rao, A. V.,Radha Krishna, P.,Yadav, J.S.
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p. 1669 - 1670
(2007/10/02)
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- ENANTIOSPECIFIC SYNTHESIS OF THE SPIROACETAL MOIETIES OF AVERMECTINS A1b, B1b, A1a, B1a, A2b, B2b, A2a, AND B2a AND MILBEMYCINS α7 AND α8
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Three differently substituted unsaturated spiroacetals, two of which form part of the structure of avermectins A1b, B1b, A1a, and B1a, have been prepared by reaction of the appropriately substituted and chiral lithium acetylide with dibenzyl protected (4S,6S)-4-hydroxy-6-hydroxymethyltetrahydropyran-2-one followed by partial hydrogenation and acid-catalysed cyclisation.The preparation of the chiral hydroxyacetylene derivatives is described.Hydration of the double bond via the chlorohydrin followed by tributyltin hydride reduction led to formation of the spiroacetal moiety found in avermectins A2b, B2b, A2a, and B2a.Epoxidation of one of the unsaturated spiroacetals and subsequent treatment with perchloric acid afforded a diaxial spiroacetal diol from the major epoxide.A protocol for the selective acylation of the diol has been developed which involves selective deprotection of the corresponding dimethyl t-butylsilylated diol under acid-catalysed conditions followed by acylation with the appropriate chiral acid chloride.Desilylation then gave the spiroacetal moiety found in milbemycins α7 and α8.The acyl chloride has been prepared by alkylation of a chiral oxazolidone with subsequent hydrolytic removal of the chiral auxiliary and reaction with oxalyl chloride.
- Baker, Raymond,Head, John C.,Swain, Christopher J.
-
-
- 2,5,6,7-tetranor-4,8-inter-m-phenylene PGI2 derivatives
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Disclosed herein are novel prostaglandin I2 (PGI2) derivatives exhibiting excellent in vivo duration and activities, said derivatives being represented by the general formula: STR1 wherein R1, X, R2 and R3 are as defined herein.
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-
- AN EFFICIENT SYNTHETIC METHOD OF METHYL (+/-)-JASMONATE
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An efficient synthetic method of methyl (+/-)-jasmonate is described. 2-Pentynyl-2-cyclopentenone, the key intermediate in this route, was synthesized by applying the palladium-catalyzed enone formation from allyl β-keto carboxylate as a key reaction.
- Kataoka, Hideaki,Yamada, Toshiro,Goto, Kuniaki,Tsuji, Jiro
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p. 4107 - 4112
(2007/10/02)
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- ORGANOPALLADIQUES ISSUS DES ESTERS D'ALCOOLS α-ALLENIQUES: REACTIONS AVEC LES ANIONS DELOCALISES.
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The esters of α-allenic alcohols, and particularly the phosphates, react in the presence of catalytic amounts of a palladium(O) complex with the anions of β-diesters, β-ketoesters and α-phenylsulfonylesters, leading by a direct substitution to β-difunctionalized allenes.This reaction can be applied to the fast obtention of an intermediate of the synthesis of the pheromone of dried bean beetle.
- Djahanbini, Dariouche,Cazes, Bernard,Gore, Jaques
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p. 3441 - 3452
(2007/10/02)
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- ENANTIOMERIC SYNTHESIS OF 6(R), 7(R) AND 6(S), 7(S) TRANS-AND CIS-LAUREDIOL
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The title compounds have been synthesized by using acetylenic coupling procedures, asymmetric epoxidation and stereo- and regio-selective openings of the epoxides.
- Anorbe, B.,Martin, V. S.,Palazon, J. M.,Trujillo, J. M.
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p. 4991 - 4994
(2007/10/02)
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- ANHYDROUS FERRIC CHLORIDE DISPERSED ON SILICA GEL INDUCED RING ENLARGEMENT OF TERTIARY CYCLOALKANOLS II: A CONVENIENT HOMOLOGATION OF CYCLOALKANONES, PREPARATION OF SPIRO SYSTEMS AND PROPELLA-γ-LACTONES
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The reagent obtained by mixing anhydrous FeCl3 and silica gel induced, in the lack of any solvent, dehydration of tertiary cycloalkanols, specific C4-->C5 and C5-->C6 ring enlargement, formation of spiro compounds and propella-γ-lactones and cleavage of tetrahydropyranyl ethers.
- Fadel, A.,Salaun, J.
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p. 1267 - 1276
(2007/10/02)
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- Synthesis of 7-Ethyl-5-methyl-4E,8E-undecadien-3-one
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Catalytic hydrogenation of 2-pentyn-1-ol (II) over Lindlar's catalyst provides 2Z-penten-1-ol (III) which on oxidation with pyridinium chlorochromate followed by Grignard reaction with ethylmagnesium bromide furnishes the carbinol (V).The vinyl ether (VI) of V on Claisen rearrangement yields 3-ethyl-4E-hepten-1-al (VII) which on Grignard reaction with methylmagnesium iodide followed by oxidation of alcohol (VIII) gives the ketone (IX), Grignard reaction on IX with vinylmagnesium bromide affords the alcohol (X).Conversion of X into the acetate (XI) followed by saponofication furnishes 5-ethyl-3-methyl-2E,6E-undecadien-1-ol (XII).XII on oxidation followed by Grignard reaction of the resulting aldehyde (XIII) with ethylmagnesium bromide produces the alcohol (XIV), which on oxidation gives the title compound.
- Vig, O. P.,Vig, R.,Dua, D. M.,Puri, S. K.
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p. 1126 - 1128
(2007/10/02)
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- Manufacture of 2-(alkyl, alkenyl or alkynyl) 3-carbalkoxyalkyl ketones from alpha, beta-unsaturated ketones
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The copper enolate of 3-allylcyclopentanone is alkylated with an alkyne so as to form the 2-alkynyl, 3-allylcyclopentanone which is then subjected to ozonolysis and oxidative cleavage to form 2-alkynylcyclopentan-3-one-1-yl alkylcarboxlic acid. The acid can be esterified to form a 2-alkynyl-3-carbalkoxyalkyl ketone which, in turn, can be hydrogenated to convert the alkynyl moiety to alkenyl or alkyl moieties. The procedure is particularly useful in the synthesis of methyl dl-jasmonate, dehydrojasminate and dihydrojasmonate.
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- Akenyl(or alkynyl) 9-xanthenyl ether compounds
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The compounds are alkenyl(and alkynyl) 9-xanthenyl ethers, for example allyl 9-xanthenyl ether, which are inhibitors of gastric acid secretion.
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