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Issue 21, 2018
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Total synthesis of complex alkaloids by nucleophilic addition to amides

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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.

Graphical abstract: Total synthesis of complex alkaloids by nucleophilic addition to amides

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Article information


Submitted
28 Mar 2018
Accepted
17 Apr 2018
First published
18 Apr 2018

Org. Biomol. Chem., 2018,16, 3864-3875
Article type
Review Article

Total synthesis of complex alkaloids by nucleophilic addition to amides

T. Sato, M. Yoritate, H. Tajima and N. Chida, Org. Biomol. Chem., 2018, 16, 3864
DOI: 10.1039/C8OB00733K

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