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Total synthesis of brevetoxin A.

ABSTRACT: A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2640830 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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Total synthesis of brevetoxin A.

Crimmins Michael T MT Zuccarello J Lucas JL Ellis J Michael JM McDougall Patrick J PJ Haile Pamela A PA Parrish Jonathan D JD Emmitte Kyle A KA

Organic letters 20090101 2

A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation. ...[more]

PMID: 19099481

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