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Letter

Selective Synthesis of (2Z,4E)-Dienyl Esters by Ene−Diene Cross Metathesis^†

Supporting Info

Gustavo Moura-Letts and Dennis P. Curran*

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260

Org. Lett., 2007, 9 (1), pp 5–8

DOI: 10.1021/ol062017d

Publication Date (Web): December 5, 2006

†

Dedicated to Professor Steven M. Weinreb on the occasion of his 65th birthday.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, curran@pitt.edu

Abstract

Cross metathesis of terminal alkenes with methyl (2Z,4E)-hexadienoate and related dienyl esters provides substituted (2Z,4E)-dienyl esters in good yields. Small-scale reactions are effectively promoted by the standard second-generation Grubbs−Hoveyda catalyst (GH-II), while a new fluorous GH-II catalyst is used for separation and recovery in gram-scale reactions. The transformation is featured in a rapid synthesis of the bottom fragments of the potent anticancer agents (−)-dictyostatin and 6-epi-dictyostatin.

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History

Published In Issue January 04, 2007
Received August 15, 2006

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Letter

Selective Synthesis of (2Z,4E)-Dienyl Esters by Ene−Diene Cross Metathesis^†