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Zhao S , Andrade RB
Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (-)-Aspidospermidine, (-)-Tabersonine, and (-)-Vincadifformine
J Org Chem. 2017 Jan 6;82(1) :521-531
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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.
Notes
1520-6904 Zhao, Senzhi Andrade, Rodrigo B ORCID: http://orcid.org/0000-0002-4554-8323 Journal Article United States J Org Chem. 2017 Jan 6;82(1):521-531. doi: 10.1021/acs.joc.6b02551. Epub 2016 Dec 12.