Selective Synthesis of (2Z,4E)-dienyl Esters by Ene-diene Cross Metathesis

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2006 Dec 29

PMID 17192071

Citations 7

Authors

Gustavo Moura-Letts

Dennis P Curran

Affiliations

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Abstract

[reaction: see text] 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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