A concise entry to the skeleton of the tremulane sesquiterpenes is described that culminated in the first enantioselective syntheses of tremulenediol A and tremulenolide A. 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] ...