Enantioselective Total Synthesis of the Diterpene (+)-Cubitene

Authors


  • Financial support by the Deutsche Forschungsgemeinschaft (DFG, Li 597/4–1) and the Fonds der Chemischen Industrie (FCI, stipend to J.W.) is gratefully acknowledged. We also thank Merck KGaA (Germany) for chromatography materials. BASF AG and Honeywell Specialty Chemicals Seelze GmbH are thanked for the donation of solvents.

Abstract

original image

From termite soldier's secretions: The enantioselective total synthesis of the diterpene (+)-cubitene is described. The route is characterized by the cyclization of a carvone-derived C20 allylphosphate with SmI2, followed by fragmentation to the twelve-membered ring. As a result, perfect stereocontrol of the isopropenyl-substituted positions is achieved.

Ancillary