A unified and biomimetic approach toward the furanocembranoids

ORGN 696

Paul A. Roethle, roethle@berkeley.edu, Department of Chemistry, University of California-Berkeley, 610 Latimer Hall, College of Chemistry, Berkeley, CA 94720 and Dirk Trauner, trauner@cchem.berkeley.edu, Center for New Directions in Organic Synthesis - Department of Chemistry, University of California, Berkeley, 602 Latimer Hall, Berkeley, CA 94720-1460.
The furanocembranoids are a large class of diterpene natural products that exhibit a wide range of interesting biological activity, including irreversible inhibition of the nicotinic acetylcholine receptor and cytotoxicity against several cancer cell lines. Our interest in this class stems from the potential to explore the biosynthetic relationships among the natural products. Bipinnatin J is a prototypical furanocembranoid that could be a key intermediate in the biosynthesis of several members of the family and in particular the recently isolated intricarene. An expedient synthesis of bipinnatin J and its biomimetic conversion to intricarene will be described.

 

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