Progress toward the total synthesis of the α-adrenergic blocking agent dispegatrine as well as the first enantiospecific total synthesis of lochvinerine, (+)-16-episarpagine, and lochnerine

ORGN 748

Chitra R. Edwankar, csawant@uwm.edu, Rahul V. Edwankar, edwankar@uwm.edu, and James M. Cook, capncook@uwm.edu. Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer St., Milwaukee, Milwaukee, WI 53211
Spegatrine and its dimer diespegatrine (1) belong to the sarpagine class of indole alkaloids.They have been reported to exhibit α-adrenergic blocking activity. The affinity of dispegatrine at α1 and α2-adrenoreceptors is about an order of magnitude larger than that of spegatrine. The enantiospecific total synthesis of monomers lochvinerine, (+)-16-Episarpagine and lochnerine as well as progress toward the total synthesis of the dimer (1) 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