4.8 Article

Unified Total Synthesis of Stemoamide-Type Alkaloids by Chemoselective Assembly of Five-Membered Building Blocks

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 50, Pages 18386-18391

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b10944

Keywords

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Funding

  1. MEXT [15K05436]
  2. Tobe Maki Foundation
  3. JSPS fellowship [15J05926]
  4. Grants-in-Aid for Scientific Research [15J05926, 26288018, 15K05436] Funding Source: KAKEN

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A unified total synthesis of stemoamide-type alkaloids is reported. Our synthetic approach features the chemoselective convergent assembly of five-membered building blocks via stemoamide as the common precursor to tetracyclic natural products. The synthesis consists of two successive coupling reactions of the three five-membered building blocks. The first coupling reaction is the vinylogous Michael addition/reduction sequence, which enables the gram-scale synthesis of stemoamide. The second coupling reaction is a chemoselective nucleophilic addition to stemoamide. While the lactone-selective nucleophilic addition to stemoamide affords saxorumamide and isosaxorumamide, the lactam-selective reductive nucleophilic addition leads to the formation of stemonine. Both chemoselective nucleophilic additions enable direct modification of stemoamide, resulting in highly concise and efficient total syntheses of the stemoamide-type alkaloids.

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