Frederick Cohen,Larry E. Overman,* andSylvie K. Ly Sakata
Department of Chemistry, 516 Rowland Hall, University of California, Irvine,
Irvine, California 92697-2025
leoverma@uci.edu
Received November 22, 1999
Abstract:
The first enantioselective total synthesis of a batzelladine alkaloid is described. The central reaction in the synthesis of (-)-batzelladine D (2)
is a tethered Biginelli condensation of a guanidine aldehyde and an acetoacetic ester to generate a 7-substituted-1-iminohexahydropyrrolo[1,2-c]pyrimidine intermediate having the anti stereochemistry of the methine hydrogens flanking the pyrrolidine nitrogen.
