Fluorous synthesis of yuehchukene by α-lithiation of perfluoroalkyl-tagged 1-(arylsulfonyl)indole with mesityllithium

Hiroshi Naka, Yusuke Akagi, Kyoko Yamada, Tatsushi Imahori, Takahiro Kasahara, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

Lithiation chemistry has not been well explored in fluorous synthesis because of the lack of appropriate base-resistant fluorous tags; we recently developed a perfluoroalkylated arylsulfonyl tag for the protection of the indole ring nitrogen atom. Mesityllithium was found to be a suitable reagent for the α-lithiation of perfluoroalkyl-tagged 1-(arylsulfonyl)indole, and the fluorous synthesis of yuehchukene was accomplished efficiently using this method as a key step.

Original languageEnglish
Pages (from-to)4635-4637
Number of pages3
JournalEuropean Journal of Organic Chemistry
Issue number28
DOIs
Publication statusPublished - 2007 Oct 19

Keywords

  • Fluorous solid-phase extraction
  • Fluorous tags
  • Indole alkaloids
  • Lithiation
  • Yuehchukene

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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