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A general enantioselective route to the chamigrene natural product family.

ABSTRACT: Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and ?-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented.

SUBMITTER: White DE

PROVIDER: S-EPMC2925317 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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A general enantioselective route to the chamigrene natural product family.

White David E DE Stewart Ian C IC Seashore-Ludlow Brinton A BA Grubbs Robert H RH Stoltz Brian M BM

Tetrahedron 20100301 26

Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, a ...[more]

PMID: 20798895

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