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

Gustavo Moura-Letts, Dennis P. Curran

Research output: Contribution to journalArticle

58 Citations (Scopus)

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

Fingerprint

metathesis
dienes
esters
Esters
catalysts
Catalysts
Alkenes
synthesis
Antineoplastic Agents
alkenes
recovery
fragments
Recovery
dictyostatin

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis. / Moura-Letts, Gustavo; Curran, Dennis P.

In: Organic Letters, Vol. 9, No. 1, 04.01.2007, p. 5-8.

Research output: Contribution to journalArticle

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