1237493-57-0Relevant academic research and scientific papers
The catalytic asymmetric total synthesis of elatol
White, David E.,Stewart, Ian C.,Grubbs, Robert H.,Stoltz, Brian M.
, p. 810 - 811 (2008)
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. Copyright
A general enantioselective route to the chamigrene natural product family
White, David E.,Stewart, Ian C.,Seashore-Ludlow, Brinton A.,Grubbs, Robert H.,Stoltz, Brian M.
experimental part, p. 4668 - 4686 (2010/08/13)
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 α-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.
