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

作者：Zheng Jian Feng; Xie Zhi Qiang; Chen Xin Jian; Huang Pei Qiang

来源：Acta Chimica Sinica, 2015, 73(7): 705-715.

DOI：10.6023/A15060395

• amides
• one-pot reaction
• cycloaddition reaction
• activation
• triflic anhydride
• alkaloids

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.

• 出版日期2015-7-15
• 单位厦门大学