70095-33-9Relevant academic research and scientific papers
Lipase catalysed resolution of (R)- and (S)-1-trimethylsilyl-1-alkyn-3-ols: Useful intermediates for the synthesis of optically-active γ-lactones
Allevi, Pietro,Ciuffreda, Pierangela,Anastasia, Mario
, p. 93 - 99 (1997)
Various (R)-and (S)-1-trimethylsilyl-1-alkyn-3-ols; chiral building units useful for the synthesis of biologically active compounds, have been efficiently resolved by enantioselective acetylation mediated by immobilized lipase PS. The resolution is applied to the synthesis of (R)- and (S)-5-octyl-2-(5H)-furanones.
Enantioselective Synthesis and Antifungal Activity of C18 Polyacetylenes
Ding, Shengli,Feng, Jiayang,Li, Changkai,Li, Honglian,Li, Qing X.,Liu, Jia,Lu, Shichao,Na, Risong,Pei, Yiming,Wang, Wenliang,Zhang, Meng
, p. 2116 - 2123 (2020/03/06)
Fungal pathogens cause serious crop diseases and decrease crop yields and quality. Polyacetylene alcohols are plant secondary metabolites and bioactive against various pathogenic fungi. They are, however, difficult to synthesize. In the present study, an efficient and highly enantioselective method (>98% ee) was established and employed to achieve the synthesis of the natural C18 polyacetylenes (S,E)-octadeca-1,9-dien-4,6-diyn-3-ol 1, (3R,10R,E)-octadeca-1,8-dien-4,6-diyne-3,10-diol 2, and their analogs. The title compounds were structurally characterized and biologically evaluated for fungicidal activities. The compounds exhibited high potencies against eight pathogenic fungal species tested, such as Colletotrichum gloeosporioiles, Bipolaris sorokiniana, Fusarium graminearum, and Fusarium pseudograminearum, with half-maximum effective concentrations ranging from 8 to 425 μg/mL, being similar to those of the fungicide thiophanate-methyl (3-408 μg/mL). These compounds are potential natural fungicides and fungicide lead candidates for further structural and property improvements.
Chemoenzymatic total synthesis of paecilocin A and 3-butyl-7- hydroxyphthalide
Sreelakshmi, Ch.,Bhaskar Rao,Lakshmi Narasu,Janardhan Reddy,Reddy, B.V. Subba
, p. 1303 - 1305 (2014/03/21)
A highly enantioselective total synthesis of paecilocin A and 3-butyl-7-hydroxyphthalide is described. The key steps involved in this synthesis are enzymatic kinetic resolution and Alder-Rickert reaction.
Pheromone synthesis. Part 249: Syntheses of methyl (R,E)-2,4,5- tetradecatrienoate and methyl (2E,4Z)-2,4-decadienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)
Mori, Kenji
experimental part, p. 1936 - 1946 (2012/04/10)
The enantiomers of methyl (E)-2,4,5-tetradecatrienoate (1), a component of the male pheromone of Acanthoscelides obtectus, were synthesized from the enantiomers of 1-undecyn-3-ol (6), which were obtained via asymmetric acetylation of (±)-1-trimethylsilyl-1-undecyn-3-ol (4) with vinyl acetate as catalyzed by lipase PS (Amano). The ortho ester Claisen rearrangement of 6 with triethyl orthoacetate was the key-step to generate the chiral allenic system. A new synthesis of (±)-1 was also executed starting from (±)-6. Three different syntheses of methyl (2E,4Z)-2,4-decadienoate (2), another component of the male pheromone of A. obtectus, were achieved by means of either palladium-catalyzed Heck reaction or a Claisen and an Al 2O3 catalyzed thermal rearrangements.
An 1,2-Elimination Approach to the Enantioselective Synthesis of 1,3-Disubstituted Linear Allenes
Zhang, Yan,Hao, Hong-Dong,Wu, Yikang
supporting information; experimental part, p. 905 - 908 (2010/08/05)
The construction of 1,3-disubstituted allene skeleton, which is present in many natural allenes, via an i-PrMgBr-mediated elimination of optically active 3-acetoxy-2-iodo-prop-1-ene derviatives is exemplified through the enantioselective total synthesis o
Efficient synthesis of optically active 2,3-allenols via the simple CuBr-mediated reaction of optically active propargylic alcohols with paraformaldehyde
Ma, Shengming,Hou, Hairong,Zhao, Shimin,Wang, Guangwei
, p. 1643 - 1645 (2007/10/03)
Enantiomerically enriched 2,3-allenols were prepared by the CuBr-mediated homologation of the relatively easily available optically active terminal propargylic alcohols with paraformaldehyde in the presence of diisopropylamine.
New synthesis of leukotriene B3 methyl ester from bis(trimethylsilyl) unsaturated derivatives
Babudri, Francesco,Fiandanese, Vito,Hassan, Omar,Punzi, Angela,Naso, Francesco
, p. 4327 - 4336 (2007/10/03)
A new synthesis of leukotriene B3 methyl ester is reported starting from bis(trimethylsilyl) unsaturated derivatives as building blocks for the triene moiety of the leukotriene. The two stereogenic centers have been generated by enantioselective chemical reduction of two acetylenic ketones with both R- or S-Alpine Borane. The three conjugated double bonds system of the leukotriene has been assembled by Miyaura-Suzuki cross-coupling reaction.
Candida antarctica Lipase B Catalysed Kinetic Resolutions: Substrate Structure Requirements for the Preparation of Enantiomerically Enriched Secondary Alcanols
Orrenius, Christian,Oehrner, Niklas,Rotticci, Didier,Mattson, Anders,Hult, Karl,Norin, Torbjoern
, p. 1217 - 1220 (2007/10/02)
The lipase B of the Candida antarctica yeast displays high enantioselectivity in transesterification reactions with chiral secondary alcohols in non-aqueous media.This was exploited to resolve a series of racemates structurally related to 2-octanol, namely 3-hydroxy-1-undecyne, 3-hydroxy-1-nonene, 3-nonanol, 1-chloro-2-octanol, 2-methyl-3-nonanol, 2,2-dimethyl-3-nonanol.The substrates were designed to probe the alcohol binding part of the active site of the lipase.The first four racemates could be resolved to produce compounds of high enantiomeric purity.A lipase catalysed transesterification of 1-chloro-2-octanol was observed. 2-Methyl-3-nonanol and 2,2-dimethyl-3-nonanol did not form any detectable amounts of product ester.The kinetic resolutions of the alcohols were performed with S-ethyl thiooctanoate as the acyl donor.
AN EFFECTIVE, PRACTICAL METHOD FOR THE SYNTHESIS OF CHIRAL PROPARGYL ALCOHOLS
Yadav, J. S.,Deshpande, Prasad K.,Sharma, G. V. M.
, p. 7033 - 7046 (2007/10/02)
The preparation of chiral propargyl alcohols (2) is described by LiNH2 or LDA induced double elimination of chiral epoxychlorides (4), derived from their corresponding epoxyalcohols (3) which are available easily by Sharpless asymmetric epoxidation of the primary allyl alcohols.Whereas, use of stoichiometric amount of base on 4 provides chirally enriched trans-1-chlorovinyl alcohols (14).
