Approach to Fully Substituted Cyclic Nitrones from N-Hydroxylactam Derivatives: Development and Application to the Total Synthesis of Cylindricine C

Shobu Hiraoka, Tsutomu Matsumoto, Koki Matsuzaka, Takaaki Sato, Noritaka Chida

研究成果: Article査読

8 被引用数 (Scopus)

抄録

An approach to cyclic nitrones from N-hydroxylactam derivatives is documented. The nucleophilic addition of an organolithium reagent to an N-OSEM [SEM=2-(trimethylsilyl)ethoxymethyl] lactam forms a five-membered chelated intermediate, which undergoes both elimination and deprotection to give a fully substituted nitrone in a one-pot process. When combined with the N-oxidation of easily available chiral lactams, this method becomes especially useful for the quick synthesis of chiral nitrones in enantio-pure form, enabling the concise total synthesis of cylindricine C.

本文言語English
ページ(範囲)4381-4385
ページ数5
ジャーナルAngewandte Chemie - International Edition
58
13
DOI
出版ステータスPublished - 2019 3 22

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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