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The catalytic asymmetric total synthesis of elatol.

ABSTRACT: Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-closing olefin metathesis to concomitantly form the spirocyclic core as well as the fully substituted chlorinated olefin. This strategy represents a general platform for accessing the chamigrene natural product family, as demonstrated by the synthesis of (+)-laurencenone B as an intermediate in our route.

SUBMITTER: White DE

PROVIDER: S-EPMC2533138 | biostudies-literature | 2008 Jan

REPOSITORIES: biostudies-literature

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The catalytic asymmetric total synthesis of elatol.

White David E DE Stewart Ian C IC Grubbs Robert H RH Stoltz Brian M BM

Journal of the American Chemical Society 20071229 3

Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-closing olefin metathesis to concomitantly form the spirocyclic core as well as the fully substituted chlorinated olefin. This strategy represents a general platform for accessing the chamigrene natural ...[more]

PMID: 18163634

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