Abstract
Abstract 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 ( 12 ) was realized via a Tollens reaction from N a -methylvellosimine ( 13 ) in 95% yield. This approach could also be applied to the synthesis of many other indole alkaloids that contain a quaternary carbon center at C(16).
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