The Catalytic Asymmetric Total Synthesis of Elatol
journal contributionposted on 23.01.2008, 00:00 by David E. White, Ian C. Stewart, Robert H. Grubbs, Brian M. Stoltz
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.