Issue 1, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Zhi-Bo Zhang,a   Zhi-Min Wang,*a   Yu-Xiu Wang,a   Huan-Quan Liu,a   Gui-Xin Leia  and  Min Shi*a  

* Corresponding authors

a Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, China

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.

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Article information

DOI
https://doi.org/10.1039/A907396E
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

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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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