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Total syntheses of (+)-vigulariol and (-)-sclerophytin A.

ABSTRACT: The total syntheses of (+)-vigulariol and (-)-sclerophytin A are reported in 15 steps and 16 steps, respectively, from a known compound. The flexible, readily scalable synthetic strategy allows for rapid construction of a critical tricyclic intermediate and is demonstrated via the synthesis of these two marine natural products. A key reaction in this synthetic protocol is a combination Wittig/intramolecular Diels-Alder cycloaddition.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC3170452 | biostudies-other | 2011 Sep

REPOSITORIES: biostudies-other

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Total syntheses of (+)-vigulariol and (-)-sclerophytin A.

Crimmins Michael T MT Stauffer Christina S CS Mans Mark C MC

Organic letters 20110819 18

The total syntheses of (+)-vigulariol and (-)-sclerophytin A are reported in 15 steps and 16 steps, respectively, from a known compound. The flexible, readily scalable synthetic strategy allows for rapid construction of a critical tricyclic intermediate and is demonstrated via the synthesis of these two marine natural products. A key reaction in this synthetic protocol is a combination Wittig/intramolecular Diels-Alder cycloaddition. ...[more]

PMID: 21853968

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