Acta Chim. Sinica ›› 2015, Vol. 73 ›› Issue (7): 705-715.DOI: 10.6023/A15060395 Previous Articles     Next Articles


酰胺的直接转化:仲酰胺与丹尼谢夫斯基双烯的还原环加成反应 2016 Awarded

郑剑峰, 谢志强, 陈欣健, 黄培强   

  1. 福建省化学生物学重点实验室 厦门大学化学化工学院化学生物学系 厦门 361005
  • 投稿日期:2015-06-06 发布日期:2015-06-15
  • 通讯作者: 郑剑峰, 黄培强;
  • 基金资助:

    项目受国家自然科学基金(No. 21332007)、国家基础科学人才培养基金(No. J1310024)、中央高校基本科研业务费专项资金(No. 20720150048)以及教育部长江学者和创新团队发展计划的资助.

Direct Transformation of Amides: Reductive Cycloaddition of Secondary Amides with Danishefsky Diene

Jian-Feng Zheng, Zhi-Qiang Xie, Xin-Jian Chen, Pei-Qiang Huang   

  1. Fujian Provincial Key Laboratory of Chemical Biology, Department of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005
  • Received:2015-06-06 Published:2015-06-15
  • Supported by:

    Supporting information for this article is available free of charge via the Internet at http://sioc-journal.cnProject supported by the National Natural Science Foundation of China (No. 21332007), National Found For Fostering Talents Of Basic Science (No. J1310024), Chinese Universities Scientific Fund (No. 20720150048) and the Program for Changjiang Scholars and Innovative Research Team in University of the Ministry of Education, China.

Amides are widely used as stable synthetic intermediates in organic synthesis and medicinal chemistry. Versatile and chemoselective C—C bond forming methods for the direct transformation of amides are highly demanding. In this paper, we report the reductive cycloaddition of common secondary amides with the Danishefsky diene to produce 2-substituted 2,3-dihydro-4-pyridones. This one-pot procedure involves amide activation with triflic anhydride, partial reduction, and [4+2] cycloaddition. The synthetic utility of this step-econimical method was demonstrated by the short and protecting-group-free total syntheses of alkaloids (±)-lasubine I and (±)-myrtine.

Key words: amides, one-pot reaction, cycloaddition reaction, activation, triflic anhydride, alkaloids