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 SmI 2 -mediated chemo- and diastereoselective reduction of the cyclopentanone.