Enantioselective Total Synthesis of the Nonisoprenoid Sesquiterpene (-)-Kumausallene.
An acyl radical cyclization to form the bicyclic core of (-)-kumausallene (1) was the key feature in the 14-step, enantioselective synthesis. This work demonstrates that the bromoallene unit is robust enough to withstand multiple synthetic operations and provides the unambiguous assignment of the absolute configuration of the bromoallene.
Evans
PA
Brown Laboratory, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716 (USA).
Murthy
VS
Roseman
JD
Rheingold
AL