Issue 1, 2000

A simple synthetic method for chiral 1,2-epoxides and the total synthesis of a chiral pheromoneepoxide

Abstract

Chiral 1,2-epoxyalkan-3-ol tosyl esters 4a–h were successfully synthesized from alkynols or allyl chlorides in three steps using Sharpless AD reaction as a key step in good yields. The chiral insect pheromone epoxide (6Z,9S,10R)-9,10-epoxyhenicos-6-ene 9 was thus smoothly synthesized from the corresponding key intermediate 4g.

Article information

Article type
Paper
Submitted
13 Sep 1999
Accepted
13 Oct 1999
First published
24 Dec 1999

J. Chem. Soc., Perkin Trans. 1, 2000, 53-57

A simple synthetic method for chiral 1,2-epoxides and the total synthesis of a chiral pheromone epoxide

Z. Zhang, Z. Wang, Y. Wang, H. Liu, G. Lei and M. Shi, J. Chem. Soc., Perkin Trans. 1, 2000, 53 DOI: 10.1039/A907396E

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