In pursuit of pestalotiopsin A via zirconocene-mediated ring contraction

ORGN 714

Shuzhi Dong, sdong@chemistry.ohio-state.edu and Leo A. Paquette, paquette.1@osu.edu. Department of Chemistry, The Evans Chemical Laboratories, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210
An asymmetric route from the α–hydroxy ester to the densely functionalized enantiopure cyclobutanol has been devised. The strategy is based on the zirconocene-mediated deoxygenative ring contraction. The cyclobutanol has been transformed into the advanced intermediate possessing all the skeletal carbons of pestalotiopsin A.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

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