32975-46-5Relevant articles and documents
Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (-)-Aspidospermidine, (-)-Tabersonine, and (-)-Vincadifformine
Zhao, Senzhi,Andrade, Rodrigo B.
, p. 521 - 531 (2017/04/26)
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.
New Dimeric Indole Alkaloids from Stenosolen heterophyllus: Structure Determinations and Synthetic Approach
Henriques, Amelia,Kan, Christiane,Chiaroni, Angele,Riche, Claude,Husson, Henri-Philippe,et al.
, p. 803 - 811 (2007/10/02)
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.