Stereoselective Synthesis of Tabtoxinine-β-lactam by Using the Vinylogous Mukaiyama Aldol Reaction with Acetate-Type Vinylketene Silyl N,O-Acetal and α-Keto-β-lactam

Hirotaka Ejima, Fumihiro Wakita, Ryo Imamura, Takuya Kato, Seijiro Hosokawa

研究成果: Article査読

11 被引用数 (Scopus)

抄録

Stereoselective total synthesis of tabtoxinine-β-lactam has been achieved. The vinylogous Mukaiyama aldol reaction with vinylketene silyl N,O-acetal and α-keto-β-lactam proceeded to afford the adduct possessing a TβL-skeleton with a tert-alcohol in high yield and stereoselectivity. Stereoselective introduction of the amino group has been accomplished by azidation at the α position of the imide followed by hydrogenolysis. A straightforward method to achieve the potent inhibitor of glutamine synthetase, possessing both α-hydroxy-β-lactam and α-amino acid moieties, has been established.

本文言語English
ページ(範囲)2530-2532
ページ数3
ジャーナルOrganic Letters
19
10
DOI
出版ステータスPublished - 2017 5 19

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

フィンガープリント 「Stereoselective Synthesis of Tabtoxinine-β-lactam by Using the Vinylogous Mukaiyama Aldol Reaction with Acetate-Type Vinylketene Silyl N,O-Acetal and α-Keto-β-lactam」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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