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 |
| 巻 | 74 |
| 発行部数 | 6 |
| 出版物ステータス | Published - 2016 |
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ASJC Scopus subject areas
- Organic Chemistry
これを引用
Nucleophilic addition to N-alkoxyamides : Development and application to the total synthesis of gephyrotoxin. / Satou, Takaaki; Chida, Noritaka.
：: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 巻 74, 番号 6, 2016, p. 599-610.研究成果: Review article
}
TY - JOUR
T1 - Nucleophilic addition to N-alkoxyamides
T2 - Development and application to the total synthesis of gephyrotoxin
AU - Satou, Takaaki
AU - Chida, Noritaka
PY - 2016
Y1 - 2016
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
UR - http://www.scopus.com/inward/record.url?scp=84980337063&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84980337063&partnerID=8YFLogxK
M3 - Review article
AN - SCOPUS:84980337063
VL - 74
SP - 599
EP - 610
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 6
ER -