Synthesis of the carbon framework of scholarisine a by intramolecular oxidative coupling

Tsugunori Watanabe, Nobuki Kato, Naoki Umezawa, Tsunehiko Higuchi

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Scholarisine A, isolated from the leaves of Alstonia scholaris, is a monoterpene indole alkaloid with an unprecedented cage-like structure. In this paper, preparation of the distinctive cage-like core skeleton of scholarisine A is described. The key feature of this synthetic strategy is an intramolecular oxidative coupling reaction at the late stage to construct a 10-oxa-tricyclo[5.3.1.03, 8]undecan-9-one structure fused with indolenine. Intramolecular oxidative coupling by using N-iodosuccinimide gave the carbon framework of scholarisine A in moderate yield, which is the first example of intramolecular oxidative-coupling reaction between non-activated enolate and indole. This study lays the foundation for continued investigations towards the total synthesis of scholarisine A.

Original languageEnglish
Pages (from-to)4255-4261
Number of pages7
JournalChemistry - A European Journal
Volume19
Issue number13
DOIs
Publication statusPublished - 2013 Mar 25
Externally publishedYes

Keywords

  • C-C coupling
  • cage compounds
  • heterocyclic compounds
  • natural products
  • polycyclic compounds
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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