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

Gustavo Moura-Letts; Dennis P. Curran

doi:10.1021/ol062017d

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

Gustavo Moura-Letts, Dennis P. Curran

Research output: Contribution to journal › Article › peer-review

68 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 language	English (US)
Pages (from-to)	5-8
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	1
DOIs	https://doi.org/10.1021/ol062017d
State	Published - Jan 4 2007
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

author = "Gustavo Moura-Letts and Curran, {Dennis P.}",

year = "2007",

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AU - Moura-Letts, Gustavo

AU - Curran, Dennis P.

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Y1 - 2007/1/4

N2 - (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.

AB - (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.

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

Abstract

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