Organic Letters
Organic Letters
4 years ago

Au-Catalyzed [2 + 3] Annulation of Enamides with Propargyl Esters: Total Synthesis of Cephalotaxine and Cephalezomine H

Au-Catalyzed [2 + 3] Annulation of Enamides with Propargyl Esters: Total Synthesis of Cephalotaxine and Cephalezomine H
Xian-Tao An, Xian-He Zhao, Xiang-Zhi Zhang, Ji-Yuan Du, Yu-Hua Deng, Xiao-Yan Ma, Chun-An Fan
A novel Au-catalyzed [2 + 3] annulation reaction of enamides with propargyl esters has been developed, providing a new method for expeditious assembly of synthetically useful functionalized 1-azaspiro[4.4]nonane building blocks. Based on this key annulation, strategic installation of the pivotal azaspirocyclic core, followed by constructing the benzazepine unit via Witkop cyclization, led to the divergent total syntheses of cephalotaxine and cephalezomine H.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01202

DOI: 10.1021/acs.orglett.7b01202

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