Journal of the American Chemical Society 2008-01-23

The catalytic asymmetric total synthesis of elatol.

David E White, Ian C Stewart, Robert H Grubbs, Brian M Stoltz

Index: J. Am. Chem. Soc. 130 , 810, (2008)

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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.