- 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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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.
- Zhao, Senzhi,Andrade, Rodrigo B.
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p. 521 - 531
(2017/04/26)
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- Domino Michael/Mannich/ N-alkylation route to the tetrahydrocarbazole framework of Aspidosperma alkaloids: Concise total syntheses of (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine
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We report a novel, asymmetric domino Michael/Mannich/N-alkylation sequence for the rapid assembly of the tetrahydrocarbazole framework of Aspidosperma alkaloids. This method was utilized in the concise total syntheses of classical targets (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine in 10 or 11 steps. Additional key steps include ring-closing metathesis to prepare the D-ring and Bosch-Rubiralta spirocyclization to prepare the C-ring.
- Zhao, Senzhi,Andrade, Rodrigo B.
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supporting information
p. 13334 - 13337
(2013/09/24)
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- New Dimeric Indole Alkaloids from Stenosolen heterophyllus: Structure Determinations and Synthetic Approach
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Structures of eight new dimeric indole alkaloids of the ervafoline 1-4 and ervafolidine series 5-8, isolated from Stenosolen heterophyllus (Vahl) Mgf (Apocynaceae), were investigated by use of mass spectrometry, 1H and 13C nuclear magnetic resonance, and X-ray crystallography.A biogenetic pathway was proposed to take into account the formation of these unusual alkaloids, and, finally, a synthetic approach based on this proposal has been developed.
- Henriques, Amelia,Kan, Christiane,Chiaroni, Angele,Riche, Claude,Husson, Henri-Philippe,et al.
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p. 803 - 811
(2007/10/02)
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