Protecting-Group-Free Formal Synthesis of Aspidospermidine: Ring-Opening Cyclization of Spirocyclopropane with Amine Followed by Regioselective Alkylations

Hisanori Nambu*, Takafumi Tamura, Takayuki Yakura

*この論文の責任著者

研究成果: ジャーナルへの寄稿学術論文査読

18 被引用数 (Scopus)

抄録

A concise formal synthesis of (±)-aspidospermidine via Stork's intermediate, which could be used as a divergent synthesis of Aspidosperma alkaloids, was achieved by employing a ring-opening cyclization of spirocyclopropane with amine followed by a regioselective intramolecular/intermolecular alkylation sequence. Stork's intermediate was synthesized in only six steps from a simple starting material, 1,3-cyclohexanedione, and was converted into (±)-aspidospermidine. To the best of our knowledge, this synthesis of Stork's intermediate involves the least number of steps to date. Furthermore, no protecting groups were used during this synthesis.

本文言語英語
ページ(範囲)15990-15996
ページ数7
ジャーナルJournal of Organic Chemistry
84
24
DOI
出版ステータス出版済み - 2019/12/20

ASJC Scopus 主題領域

  • 有機化学

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