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

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Lewis Acids
Addition reactions
Antimalarials
Ketones
Derivatives
Acids
Substrates
piperidine
febrifugine

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition. / Sukemoto, Satoshi; Oshige, Miyo; Sato, Masahiro; Mimura, Ken Ichiro; Nishioka, Hiromi; Abe, Hitoshi; Harayama, Takashi; Takeuchi, Yasuo.

In: Synthesis, No. 19, F10608SS, 01.10.2008, p. 3081-3087.

Research output: Contribution to journalArticle

Sukemoto, Satoshi ; Oshige, Miyo ; Sato, Masahiro ; Mimura, Ken Ichiro ; Nishioka, Hiromi ; Abe, Hitoshi ; Harayama, Takashi ; Takeuchi, Yasuo. / Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition. In: Synthesis. 2008 ; No. 19. pp. 3081-3087.
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AU - Abe, Hitoshi

AU - Harayama, Takashi

AU - Takeuchi, Yasuo

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