有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
総説および総合論文
N-アルコキシアミド基への求核付加反応の開発とゲフィロトキシンの全合成
佐藤 隆章千田 憲孝
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74 巻 (2016) 6 号 p. 599-610

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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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© 2016 社団法人 有機合成化学協会
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