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

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4381-4385
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number13
DOIs
Publication statusPublished - 2019 Mar 22

Keywords

  • amides
  • nitrones
  • nucleophilic addition
  • synthetic methods
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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