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Studies on the identification and syntheses of insect pheromones: XX. Synthesis of (7 R , 8 S )‐(+)‐sex pheromone of gypsy moth through the kinetic resolution of (±) allylic alcohol by Sharpless asymmetric epoxidation
Author(s) -
Lin GuoQiang,
Jiang YanYing,
Zhou WeiShan
Publication year - 1985
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19850030311
Subject(s) - sex pheromone , chemistry , kinetic resolution , pheromone , insect , sharpless epoxidation , stereochemistry , alcohol , yield (engineering) , allylic rearrangement , epoxide , organic chemistry , enantioselective synthesis , botany , biology , catalysis , materials science , metallurgy
The chiral epoxy alcohol 3 was synthesized in 92% e.e through the kinetic resolution of (±)‐l‐tridecen‐3‐ol 2 by Sharpless asymmetric epoxidation. 3 was then transformed to (7 R , 8 S )‐1a, the sex pheromone of gypsy moth, in an overall yield of 60% in 5 steps.