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

Makoto Yoritate, Yoshito Takahashi, Hayato Tajima, Chisato Ogihara, Takashi Yokoyama, Yasuki Soda, Takeshi Oishi, Takaaki Sato, Noritaka Chida

研究成果: Contribution to journalArticle

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抜粋

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.

元の言語英語
ページ(範囲)18386-18391
ページ数6
ジャーナルJournal of the American Chemical Society
139
発行部数50
DOI
出版物ステータス出版済み - 12 20 2017
外部発表Yes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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