- The catalytic asymmetric total synthesis of elatol.
The catalytic asymmetric total synthesis of elatol.
Journal of the American Chemical Society (2008-01-01)
David E White, Ian C Stewart, Robert H Grubbs, Brian M Stoltz
PMID18163634
摘要
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.