229974-18-9Relevant academic research and scientific papers
An Efficient Enantioselective Synthesis of (+)-Disparlure
Hu, Shaojing,Jayaraman, Seetharaman,Oehlschlager, Allan C.
, p. 3719 - 3721 (1999)
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.
