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Updated: Feb 11, 2026

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Total synthesis of complex alkaloids by nucleophilic addition to amides
Takaaki Sato1, Makoto Yoritate, Hayato Tajima
1Department of Applied Chemistry, Faculty of Science and Technology, Keio University 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. takaakis@applc.keio.ac.jp.
Abstract:
Nucleophilic addition to amides has been recognized as a promising transformation for total synthesis of complex alkaloids. Amides can accept two different organometallic reagents through the nucleophilic addition, which enables it to serve as a stable surrogate of multi-substituted amines. However, the nucleophilic addition has been overlooked for a long time due to three main reasons: low electrophilicity of amide carbonyls, potential hydrolysis of the reaction intermediate and excess addition of an organometallic reagent. This mini review focuses on the recent progress of total synthesis of complex alkaloids based on the nucleophilic additions to N-alkoxyamides, tertiary amides and secondary amides.
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