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Toward the synthesis of (+)-peloruside A via an intramolecular vinylogous aldol reaction.

ABSTRACT: The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A is described. The reaction was applied to compound 19 and proceeds in high yield and good levels of diastereoselectivity. Application of the Achmatowicz reaction to this intermediate provided the corresponding pyranone, a late stage intermediate well positioned for conversion to the natural product.

SUBMITTER: Gazaille JA

PROVIDER: S-EPMC3272878 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Toward the synthesis of (+)-peloruside A via an intramolecular vinylogous aldol reaction.

Gazaille Jeffrey A JA Abramite Joseph A JA Sammakia Tarek T

Organic letters 20111212 1

The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A is described. The reaction was applied to compound 19 and proceeds in high yield and good levels of diastereoselectivity. Application of the Achmatowicz reaction to this intermediate provided the corresponding pyranone, a late stage intermediate well positioned for conversion to the natural product. ...[more]

PMID: 22149174

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