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

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 electrop...

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Published inJournal of organic chemistry Vol. 82; no. 1; pp. 521 - 531
Main Authors Zhao, Senzhi, Andrade, Rodrigo B
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.01.2017
Subjects
Alkaloids - chemical synthesis
Alkaloids - chemistry
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Molecular Structure
Quinolines - chemical synthesis
Quinolines - chemistry
Stereoisomerism
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02551