An Efficient Enantioselective Synthesis of (+)-Disparlure

Synthesis of (+)-disparlure, 1, the sex pheromone of gypsy moth (Lymantria dispar), commenced from cis-vinyl epoxide 4 which was prepared by our asymmetric chloroallylboration in 99% de and 94% ee. Hydroboration of 4 using dicyclohexylborane in THF, followed by sodium perborate oxidation gave a crys...

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Bibliographic Details
Published in:Journal of organic chemistry 1999-05, Vol.64 (10), p.3719-3721
Main Authors: Hu, Shaojing, Jayaraman, Seetharaman, Oehlschlager, Allan C
Format: Article
Language:English
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Summary:Synthesis of (+)-disparlure, 1, the sex pheromone of gypsy moth (Lymantria dispar), commenced from cis-vinyl epoxide 4 which was prepared by our asymmetric chloroallylboration in 99% de and 94% ee. Hydroboration of 4 using dicyclohexylborane in THF, followed by sodium perborate oxidation gave a crystalline cis-3,4-epoxy alcohol 3 whose enantiomeric purity was enhanced by recrystallization. Conversion of 3 to (+)-disparlure was via alkylation of the tosylate. (+)-Disparlure was produced in four steps with an overall yield of 27% and ≥99.5% ee.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9820871