Issue 21, 2018

Total synthesis of complex alkaloids by nucleophilic addition to amides

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

Article information

Article type
Review Article
Submitted
28 mars 2018
Accepted
17 avr. 2018
First published
18 avr. 2018

Org. Biomol. Chem., 2018,16, 3864-3875

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements