Unified approach to miscellaneous Lycopodium alkaloids: Total synthesis of (+)-lyconadin A

ORGN 790

Scott P. West, spwest@berkeley.edu, Alakesh Bisai, Andrew D. Lim, Raja R. Narayan, and Richmond Sarpong. Department of Chemistry, University of California, Berkeley, 847 Latimer Hall, Berkeley, CA 94720
A unified approach to the ‘miscellaneous' subset of Lycopodium alkaloids has been developed. A key element is the elaboration of tricyclic cycloheptadiene 3 to form the common tetracyclic intermediate 2. Our strategy has been employed to achieve the enantioselective synthesis of the pentacyclic alkaloid (+)-lyconadin A (1). The key reaction involves an oxidative cyclization to form the crucial C-N bond to complete the pentacyclic core of the lyconadins. Studies on this novel transformation have been conducted to understand the mechanism of this process.

 

Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009