|Name||Mr. Chris Cain|
|Organization or Institution||University of South Florida Chemistry|
Synthetic studies toward the 4-alkylideneproline natural products eleganine A and 17-nor-excelsinidine
Chris F. Cain, Justin A. Goodwin, Evan H. Howard, Juan R. Del Valle
University of South Florida
Eleganine A is a monoterpene indole alkaloid capable of inducing apoptosis in HuH-7 cancer cells. 17-Nor-excelsinidine, a novel member of the akuammiline family of alkaloids, possesses an unusual 1-azoniatricyclo [188.8.131.52] undecane core structure and has shown activity against adenovirus and HSV. Of interest from a synthetic standpoint, these molecules contain an alkylideneproline moiety found in only a handful of other natural products including lucentamycin A and isodomic Acids G and H. Here, we describe our progress toward the total synthesis of eleganine A and 17-nor-excelsinidine starting from L-serine as a chiral progenitor. Our synthetic strategy involves formation of the ethylidene proline fragment via nickel-catalyzed reductive Heck-type cyclization and generation of the indole ring through Larock heteroanulation.