The first enantiospecific total synthesis of the 3-oxygenated sarpagine indole alkaloids affinine and 16-epiaffinine

ORGN 783

Jie Yang, yang49@uwm.edu, Sundari K Rallapalli, sundari@uwm.edu, and James M Cook, capncook@uwm.edu. Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer St., Milwaukee, WI 53211
Affinine (1) was first isolated from Peschiera affinis (Apocynaceae) while 16-epiaffinine (2) was isolated from the bark of Pleiocarpa talbotii. These indole alkaloids belong to the class of 3-oxygenated sarpagine indole alkaloids. Affinine and 16-epiaffinine both showed moderate antibacterial activity against several human pathogens. The first enantiospecific total synthesis of these indole alkaloids will be presented.

 

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