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 | Zendy

Lin GuoQiang | Zendy; Jiang YanYing | Zendy; Zhou WeiShan | Zendy

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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.

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