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Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent.

ABSTRACT: An enantioselective total synthesis of zampanolide has been accomplished using a novel DDQ/Brønsted acid promoted cyclization as the key reaction. The synthesis features cross-metathesis to construct the trisubstituted olefin and a ring-closing metathesis to form the macrolactone. The final N-acyl aminal formation was stereoselectively accomplished by an organocatalytic reaction.

SUBMITTER: Ghosh AK

PROVIDER: S-EPMC3153378 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent.

Ghosh Arun K AK Cheng Xu X

Organic letters 20110712 15

An enantioselective total synthesis of zampanolide has been accomplished using a novel DDQ/Brønsted acid promoted cyclization as the key reaction. The synthesis features cross-metathesis to construct the trisubstituted olefin and a ring-closing metathesis to form the macrolactone. The final N-acyl aminal formation was stereoselectively accomplished by an organocatalytic reaction. ...[more]

PMID: 21749032

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