Direct Transformation of Amides: Reductive Cycloaddition of Secondary Amides with Danishefsky Diene
Received date: 2015-06-06
Online 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
Jian-Feng Zheng , Zhi-Qiang Xie , Xin-Jian Chen , Pei-Qiang Huang . Direct Transformation of Amides: Reductive Cycloaddition of Secondary Amides with Danishefsky Diene[J]. Acta Chimica Sinica, 2015 , 73(7) : 705 -715 . DOI: 10.6023/A15060395
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