Nucleophilic addition to N-alkoxyamides: Development and application to the total synthesis of gephyrotoxin

研究成果: Review article

18 引用 (Scopus)

抄録

Nucleophilic addition to amide carbonyl groups is the simplest way to access multi-substituted amines found in biologically active natural alkaloids and pharmaceuticals. However, this promising transformation has received less attention due to their high stability. In this article, we describe our recent progress with N-alkoxyamides. Incorporation of an alkoxy group as a reactivity control element into the nitrogen atom of an amide successfully overcomes issues inherent to the nucleophilic addition. Especially, chemoselective version with the Schwartz reagent was useful, and enabled the concise total synthesis of (±)-gephyrotoxin.

元の言語English
ページ(範囲)599-610
ページ数12
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
74
発行部数6
出版物ステータスPublished - 2016

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Amides
Alkaloids
Amines
Nitrogen
Atoms
Pharmaceutical Preparations
gephyrotoxin
Schwartz reagent
alkoxyl radical

ASJC Scopus subject areas

  • Organic Chemistry

これを引用

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abstract = "Nucleophilic addition to amide carbonyl groups is the simplest way to access multi-substituted amines found in biologically active natural alkaloids and pharmaceuticals. However, this promising transformation has received less attention due to their high stability. In this article, we describe our recent progress with N-alkoxyamides. Incorporation of an alkoxy group as a reactivity control element into the nitrogen atom of an amide successfully overcomes issues inherent to the nucleophilic addition. Especially, chemoselective version with the Schwartz reagent was useful, and enabled the concise total synthesis of (±)-gephyrotoxin.",
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AU - Chida, Noritaka

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N2 - Nucleophilic addition to amide carbonyl groups is the simplest way to access multi-substituted amines found in biologically active natural alkaloids and pharmaceuticals. However, this promising transformation has received less attention due to their high stability. In this article, we describe our recent progress with N-alkoxyamides. Incorporation of an alkoxy group as a reactivity control element into the nitrogen atom of an amide successfully overcomes issues inherent to the nucleophilic addition. Especially, chemoselective version with the Schwartz reagent was useful, and enabled the concise total synthesis of (±)-gephyrotoxin.

AB - Nucleophilic addition to amide carbonyl groups is the simplest way to access multi-substituted amines found in biologically active natural alkaloids and pharmaceuticals. However, this promising transformation has received less attention due to their high stability. In this article, we describe our recent progress with N-alkoxyamides. Incorporation of an alkoxy group as a reactivity control element into the nitrogen atom of an amide successfully overcomes issues inherent to the nucleophilic addition. Especially, chemoselective version with the Schwartz reagent was useful, and enabled the concise total synthesis of (±)-gephyrotoxin.

KW - Aide

KW - Chemoselectivity

KW - Gephyrotoxin

KW - Nucleophilic addition

KW - Piperidine

KW - Reactivity control

KW - Total synthesis

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