Total synthesis of complex alkaloids by nucleophilic addition to amides

Takaaki Sato, Amakoto Yoritate, Hayato Tajima, Noritaka Chida

Research output: Contribution to journalArticle

21 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3864-3875
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number21
DOIs
Publication statusPublished - Jan 1 2018
Externally publishedYes

Fingerprint

alkaloids
Alkaloids
Amides
amides
synthesis
Organometallics
reagents
Reaction intermediates
reaction intermediates
Amines
hydrolysis
Hydrolysis
amines

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Total synthesis of complex alkaloids by nucleophilic addition to amides. / Sato, Takaaki; Yoritate, Amakoto; Tajima, Hayato; Chida, Noritaka.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 21, 01.01.2018, p. 3864-3875.

Research output: Contribution to journalArticle

Sato, Takaaki ; Yoritate, Amakoto ; Tajima, Hayato ; Chida, Noritaka. / Total synthesis of complex alkaloids by nucleophilic addition to amides. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 21. pp. 3864-3875.
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