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Asymmetric total synthesis of pyranicin.

ABSTRACT: The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2826115 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Asymmetric total synthesis of pyranicin.

Crimmins Michael T MT Jacobs Danielle L DL

Organic letters 20090601 12

The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy. ...[more]

PMID: 19438254

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