Synthetic access to the hetisine alkaloids: Total synthesis of (±)-nominine

ORGN 859

David Y. Gin, gin@scs.uiuc.edu and Kevin M. Peese. Department of Chemistry, University of Illinois, Urbana-Champaign, 600 S. Mathews Ave., Urbana, IL 61801
A synthetic approach to the hetisine C-20-diterpenoid alkaloids is presented. The approach is exemplified by the 15-step total synthesis of (±)-nominine. The development of this strategy, employing an early stage aza-1,3-dipolar cycloaddition and a late stage Diels-Alder cycloaddition, is discussed.

 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 134, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006