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.