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A highly convergent approach toward (-)-brevenal.

ABSTRACT: Progress toward a highly convergent, asymmetric synthesis of brevenal is reported. Construction of the AB-ring and E-ring cyclic ether fragments was achieved through asymmetric alkylation/ring-closing metathesis strategies. A Horner-Wadsworth-Emmons olefination was used in a key bond-forming step to couple the advanced cyclic fragments and enable rapid access to the AB-E ring system.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2878377 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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A highly convergent approach toward (-)-brevenal.

Crimmins Michael T MT Shamszad Mariam M Mattson Anita E AE

Organic letters 20100601 11

Progress toward a highly convergent, asymmetric synthesis of brevenal is reported. Construction of the AB-ring and E-ring cyclic ether fragments was achieved through asymmetric alkylation/ring-closing metathesis strategies. A Horner-Wadsworth-Emmons olefination was used in a key bond-forming step to couple the advanced cyclic fragments and enable rapid access to the AB-E ring system. ...[more]

PMID: 20446718

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