Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition

Satoshi Sukemoto, Miyo Oshige, Masahiro Sato, Ken Ichiro Mimura, Hiromi Nishioka, Hitoshi Abe, Takashi Harayama, Yasuo Takeuchi

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Intramolecular conjugate addition of γ-substituted (E)- α,β-unsaturated ketones with a Lewis acid (BF3· OEt2) selectively afforded trans-2,3-disubstituted piperidine derivatives. Chiral substrates were synthesized by Sharpless asymmetric dihydroxylation of the enamine; the antimalarial compound febrifugine was synthesized from the major product of the conjugate addition reaction.

Original languageEnglish
Article numberF10608SS
Pages (from-to)3081-3087
Number of pages7
JournalSynthesis
Issue number19
DOIs
Publication statusPublished - Oct 1 2008

Keywords

  • Asymmetric synthesis
  • Febrifugine
  • Intramolecular conjugate addition
  • Lewis acid

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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