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A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

ABSTRACT: Homoallylation of aldehydes with isoprene and triethylborane catalyzed by Ni(acac)(2) gave hydroxyalkenes in good yield with excellent regio- and stereoselectivity. Cross metathesis of the hydroxyalkenes with methyl acrylate using second-generation Grubbs catalyst and copper(I) iodide afforded alpha,beta-unsaturated esters, which underwent cyclization in the presence of DBU to produce tetrahydrofurans with the correct relative configuration for the C1-C9 fragment of amphidinolides C, C2, and F.

SUBMITTER: Paudyal MP

PROVIDER: S-EPMC2896498 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

Paudyal Mahesh P MP Rath Nigam P NP Spilling Christopher D CD

Organic letters 20100701 13

Homoallylation of aldehydes with isoprene and triethylborane catalyzed by Ni(acac)(2) gave hydroxyalkenes in good yield with excellent regio- and stereoselectivity. Cross metathesis of the hydroxyalkenes with methyl acrylate using second-generation Grubbs catalyst and copper(I) iodide afforded alpha,beta-unsaturated esters, which underwent cyclization in the presence of DBU to produce tetrahydrofurans with the correct relative configuration for the C1-C9 fragment of amphidinolides C, C2, and F. ...[more]

PMID: 20527780

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