Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis

Gustavo Moura-Letts, Dennis P. Curran

Research output: Contribution to journalArticle

59 Scopus citations

Abstract

(Chemical Equation Presented) Cross metathesis of terminal alkenes with methyl (2Z4E)-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.

Original languageEnglish (US)
Pages (from-to)5-8
Number of pages4
JournalOrganic Letters
Volume9
Issue number1
DOIs
StatePublished - Jan 4 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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