Enantioselective Syntheses of
Tremulenediol A and Tremulenolide A
Brandon L. Ashfeld andStephen F. Martin*
Department of Chemistry and Biochemistry, The University of Texas at Austin,
Austin, Texas 78712
sfmartin@mail.utexas.edu
Received August 11, 2005
Abstract:
An enantioselective entry to the skeleton of the tremulane sesquiterpenes is described. The approach features a series of efficient transition
metal-catalyzed reactions commencing with an enantioselective rhodium(II)-catalyzed intramolecular cyclopropanation followed by a regioselective
allylic alkylation and a diastereoselective rhodium(I)-catalyzed [5 + 2] cycloaddition. This strategy was applied to the first enantioselective
syntheses of tremulenediol A and tremulenolide A.
