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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"