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

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.

SUBMITTER: Moura-Letts G

PROVIDER: S-EPMC2535931 | biostudies-literature | 2007 Jan

REPOSITORIES: biostudies-literature

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

Moura-Letts Gustavo G Curran Dennis P DP

Organic letters 20070101 1

[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 (-)-d ...[more]

PMID: 17192071

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