131484-41-8Relevant academic research and scientific papers
Synthesis of optically pure cis epoxyalcohols via an enzymatic route; an alternative to the sharpless asymmetric epoxidation
Grandjean,Pale,Chuche
, p. 3043 - 3046 (1991)
Optically pure (2S, 3R)-4-butyryloxy-2,3-epoxybutan-1-ol 2b and (2R, 3S)-4-tert-butyldiphenylsilyloxy-2,3-epoxybutan-1-ol 5, starting materials for the synthesis of enantiomeric epoxyalcohols 3 and 4, were obtained after enzymatic hydrolysis of meso cis-2,3-epoxybutane-1,4-diol diesters 1b.
Stereoselective total synthesis of multiplolide A and of a diastereoisomer
Reddy, Bandi Chennakesava,Bangade, Vikas Madhukar,Ramesh, Palakuri,Meshram, Harshadas Mitaram
, p. 266 - 274 (2013/03/28)
A stereoselective total synthesis of multiplolide A (1) and of its diastereoisomer 2 was described from easily accessible starting materials (Schemes 2-4). The synthetic strategy involves a Jacobsen resolution, Sharpless epoxidation, Swern oxidation, Yamaguchi reaction, and ring-closing metathesis (RCM). Copyright
Asymmetric syntheses of (-)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate
Ayad, Tahar,Genisson, Yves,Baltas, Michel
, p. 2626 - 2631 (2007/10/03)
Ready access to natural (-)-lentiginosine and its pyrrolizidinic analogue from a chiral vinylic epoxyamine in a straightforward five-step sequence is presented. Careful use of the RCM reaction on aminotriols 5 and 6 constitutes the key feature of the synt
Synthesis of all four stereoisomers of leucomalure, components of the female sex pheromone of the Satin moth, Leucoma salicis
Muto, Shin-etsu,Mori, Kenji
, p. 1300 - 1307 (2007/10/03)
Lipase PS-C (Amano)-catalyzed asymmetric acetylation of (±)-4-(tert-butyldiphenylsilyloxy)-cis-2,3-epoxy-1-butanol afforded the (2R,3S)-epoxy alcohol and the (2S,3R)-epoxyacetate, which were converted into all of the four stereoisomers of leucomalure [(3Z
Pheromone synthesis; CXXXIX. Enzymatic preparation of (2S,3R)-4-acetoxy-2,3-epoxybutan-1-ol and its conversion to the epoxy pheromones of the gypsy moth and the ruby tiger moth
Brevet,Mori
, p. 1007 - 1012 (2007/10/02)
Pig pancreatic lipase-catalyzed asymmetric hydrolysis of 1,4-diacetoxy-cis-2,3-epoxybutane yielded (2S,3R)-4-acetoxy-2,3-epoxybutan-1-ol, which was converted to two naturally occurring epoxides: the gypsy moth pheromone, disparlure [(7R,8S)-7,8-epoxy-2-methyloctadecane] and the ruby tiger moth pheromone [(6Z,9S,10R)-9,10-epoxy-6-henicosene].
APPLICATION OF BIOCHEMICAL METHODS IN ENANTIOSELECTIVE SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS
Mori, Kenji
, p. 393 - 406 (2007/10/02)
Enzymes as well as yeasts were used in enantioselective syntheses of bioregulators such as hormones and semiochemicals.Lipases and esterases were employed in achieving optical resolution, conversion of meso-compounds to optically active compounds, and macrolactonization.Lactase effected glucosidation of a phenolic hydroxy ketone without any protection of the functional groups.Yeasts provided a variety of optically active hydroxy esters and ketones, which served as versatile non-racemic chiral building blocks.
A Stereochemically General Synthesis of 2-Deoxyhexoses via the Asymmetric Allylboration of 2,3-Epoxy Aldehydes
Roush, William R.,Straub, Julie A.,VanNieuwenhze, Michael S.
, p. 1636 - 1648 (2007/10/02)
A stereochemically general strategy for the synthesis of 2-deoxyhexoses is described.This new approach involves the asymmetric allylboration of epoxy aldehydes 12 and 13, prepared via the Sharpless asymmetric epoxidation reaction, as a means of establishi
