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Enantioselective total synthesis of brevetoxin A: convergent coupling strategy and completion.

ABSTRACT: A highly convergent, enantioselective total synthesis of brevetoxin A is reported. The development of a [X+2+X] Horner-Wadsworth-Emmons/cyclodehydration/reductive etherification convergent coupling strategy allowed a unified approach to the synthesis of two advanced tetracyclic fragments from four cyclic ether subunits. The Horner-Wittig coupling of the two tetracyclic fragments provided substrates that were explored for reductive etherification, the success of which delivered a late-stage tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2826122 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Enantioselective total synthesis of brevetoxin A: convergent coupling strategy and completion.

Crimmins Michael T MT Zuccarello J Lucas JL McDougall Patrick J PJ Ellis J Michael JM

Chemistry (Weinheim an der Bergstrasse, Germany) 20090901 36

A highly convergent, enantioselective total synthesis of brevetoxin A is reported. The development of a [X+2+X] Horner-Wadsworth-Emmons/cyclodehydration/reductive etherification convergent coupling strategy allowed a unified approach to the synthesis of two advanced tetracyclic fragments from four cyclic ether subunits. The Horner-Wittig coupling of the two tetracyclic fragments provided substrates that were explored for reductive etherification, the success of which delivered a late-stage tetra ...[more]

PMID: 19655349

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