Asymmetric Total Synthesis of Rumphellclovane E.

The first asymmetric total synthesis of rumphellclovane E, a clovane-type sesquiterpenoid, has been accomplished in eight steps from commercially available (R)-carvone. Key elements of the synthesis include Rh-catalyzed cyclopropanation, iron-catalyzed intramolecular reductive aldol reaction, and SmI2-mediated chemo- and diastereoselective reduction of the cyclopentanone.