Toward a total synthesis of guanacastepene E

ORGN 697

Aubry K. Miller, aubry@berkeley.edu1, Chambers C. Hughes2, Joshua J. Kennedy-Smith3, and Dirk Trauner1. (1) Department of Chemistry, University of California, Berkeley, Berkeley, CA 94708, (2) Scripps Oceanography Institute, (3) Roche Palo Alto, Palo Alto, CA
Tetracycle 4, containing the core structure of guanacastepene E (5), has been synthesized via electrochemical oxidative cyclization of furanyl silyl enol ether 3. Cyclization precursor 3 was prepared through a diastereoselective conjugate addition of enantiomerically enriched building blocks 1 and 2. The construction of these building blocks and the endgame strategy for the total synthesis is discussed.

 

Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 132, Oral

Division of Organic Chemistry

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