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Synthesis of all Four Stereoisomers of Leucomalure, Components of the Female Sex Pheromone of the Satin Moth, Leucoma salicis
Author(s) -
Muto Shinetsu,
Mori Kenji
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390186
Subject(s) - chemistry , pheromone , sex pheromone , stereochemistry , acetylation , botany , biology , biochemistry , gene
Lipase PS‐C(Amano)‐catalyzed asymmetric acetylation of (±)‐4‐( tert ‐butyldiphenylsilyloxy)‐ cis ‐2,3‐epoxy‐1‐butanol afforded the (2 R ,3 S )‐epoxy alcohol and the (2 S ,3 R )‐epoxyacetate, which were converted into all of the four stereoisomers of leucomalure [(3 Z )‐ cis ‐6,7‐ cis ‐9,10‐diepoxy‐3‐henicosene], the female sex pheromone of the Satin moth, Leucoma salicis . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)