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J Org Chem


Title:An Efficient Enantioselective Synthesis of (+)-Disparlure
Author(s):Hu S; Jayaraman S; Oehlschlager AC;
Address:"Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6"
Journal Title:J Org Chem
Year:1999
Volume:64
Issue:10
Page Number:3719 - 3721
DOI: 10.1021/jo9820871
ISSN/ISBN:1520-6904 (Electronic) 0022-3263 (Linking)
Abstract:"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"
Keywords:
Notes:"PubMed-not-MEDLINEHu, Shaojing Jayaraman, Seetharaman Oehlschlager, Allan C eng 2001/10/25 J Org Chem. 1999 May 14; 64(10):3719-3721. doi: 10.1021/jo9820871"

 
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