A stereochemical solution for the tetrapetalones: Diastereoselective means to the cyclohexadienone core

ORGN 896

John K. Ward, jward@chem.ucsb.edu, Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106 and Thomas R. R. Pettus, pettus@chem.ucsb.edu, Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106.
The tetrapetalone family of natural products contains a series of 4-5 contiguous stereocenters arranged about a cyclohexadienone core. Our strategy imagines the control of all stereocenters from the control of one. Attempts at initial diastereoselective control via an ortho-quinone methide intermediate will be examined. Stereoselective oxidative dearomatization as a means to complete the core as part of a model study will also be highlighted.
 

New Reactions and Methodology
8:00 AM-11:40 AM, Thursday, 14 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

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