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用于便捷构建环戊[1,2-]吡咯并[1,2-]氮杂环庚烷环系的还原型氧杂-纳扎罗夫环化反应:百部碱和三尖杉碱的形式全合成

Reductive Oxy-Nazarov Cyclization toward Expedient Construction of a Cyclopenta[1,2-]pyrrolo[1,2-]azepine Ring System: Formal Total Syntheses of Stemonamine and Cephalotaxine.

作者信息

Yan Xifei, Zhang Qin, Zheng Jianfeng, Li Wei-Dong Z

机构信息

School of Chemistry, Key Laboratory of Advanced Technologies of Material, Minister of Education, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, P. R. China.

出版信息

J Org Chem. 2024 Apr 5;89(7):5164-5169. doi: 10.1021/acs.joc.4c00035. Epub 2024 Mar 27.

Abstract

Formal total syntheses of stemonamine and cephalotaxine bearing the core cyclopenta[1,2-]pyrrolo[1,2-]azepine ring skeleton were achieved. The general synthetic strategy in the synthesis features the reductive oxy-Nazarov cyclization as key step, leading to the versatile construction of N-substituted spiro quaternary stereogenic centers from readily available starting materials.

摘要

实现了含有核心环戊并[1,2 -]吡咯并[1,2 -]氮杂环庚烷环骨架的百部碱和三尖杉碱的形式全合成。该合成中的一般合成策略以还原氧杂 - 纳扎罗夫环化反应为关键步骤,能够从易得的起始原料出发,通用地构建N - 取代的螺季碳立体中心。

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