The catalytic asymmetric total synthesis of elatol.
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.
White
David E
DE
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Stewart
Ian C
IC
Grubbs
Robert H
RH
Stoltz
Brian M
BM
D002384:Catalysis; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013141:Spiro Compounds; C526604:laurencenone B; C485576:elatol