General approach for the synthesis of 12-methoxy substitured sarpagine indole alkaloids including 12-methoxy-Nb-methylvoachalotine and fuchsiaefoline

ORGN 173

Hao Zhou and James M. Cook, capncook@uwm.edu. Department of Chemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer St., Milwaukee, WI 53210
The enantiospecific synthesis of 7-methoxy-D-tryptophan was completed by combination of the Larock heteroannulation process with a Schöllkopf based chiral auxiliary in good yield. This ester was then employed in the first total synthesis of 12-methoxy-Nb-methylvoachalotine, (+)-12-methoxy-Na-methylvellosimine, (+)-12-methoxyaffinisine and (-)-fuchsiaefoline in regiospecific, stereospecific fashion in excellent overall yield. The asymmetric Pictet-Spengler reaction and enolate- driven palladium catalyzed cross coupling processes served as key steps.

 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006