title: Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (-)-Aspidospermidine, (-)-Tabersonine, and (-)-Vincadifformine.
abstract: 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.
authors.affiliation: Department of Chemistry, Temple University , Philadelphia, Pennsylvania 19122, United States.
authors.forename: Senzhi
authors.initials: S
authors.lastname: Zhao
authors.affiliation: Department of Chemistry, Temple University , Philadelphia, Pennsylvania 19122, United States.
authors.forename: Rodrigo B
authors.identifier: 0000-0002-4554-8323
authors.initials: RB
authors.lastname: Andrade
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D026121:Indole Alkaloids; D011804:Quinolines; C409672:aspidospermidine; C456406:vincadifformine; C009373:tabersonine