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Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (−)-Aspidospermidine, (−)-Tabersonine, and (−)-Vincadifformine

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journal contribution
posted on 29.11.2016, 00:00 by Senzhi Zhao, Rodrigo B. Andrade
The development and application of the arene-fused domino Michael/Mannich route to the tetrahydrocarbazole (ABE) core of Aspidosperma alkaloids is described. The scope of this novel transformation was studied in terms of the nucleophilic component (i.e., N-sulfinyl metallodienamine) and the electrophilic component (i.e., Michael acceptor). The successful application of this methodology toward the concise total syntheses of classical indole alkaloids (−)-aspidospermidine, (−)-tabersonine, and (−)-vincadifformine in 10–11 steps, respectively, is also discussed.