Journal
ORGANIC LETTERS
Volume 6, Issue 2, Pages 249-252Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0362212
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[GRAPHICS] The enantiospecific synthesis of 7-methoxy-D-tryptophan was completed by combination of the Larock heteroannulation process with a Schollkopf-based chiral auxiliary in good yield. This ester was then employed in the first total synthesis of (+)-12-methoxy-N-a-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.
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