ORGN 439 |
First enantiospecific total synthesis of a quaternary voachalotine alkaloid, (+)-dehydrovoachalotine
| Jianming Yu, Jun Ma, Xiangyu Wearing, and James M. Cook. Department of Chemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, WI 53201 |
The first enantiospecific total synthesis of the indole alkaloid (+)-dehydrovoachalotine (1) has been achieved from D-(+)-tryptophan methyl ester in 28% overall yield. The formation of the prochiral quaternary carbon center at C-16 in the key intermediate (2) was realized via a Tollens' reaction from Na-methylvellosimine in 95% yield. This approach could also be applied to the synthesis of many other indole alkaloids which contain a quaternary carbon center at C(16).  |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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