Total synthesis of dl-febrifugine and dl-isofebrifugine

Yasuo Takeuchi, Hitoshi Abe, Takashi Harayama

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Racemic compounds (1 and 2) of the antimalarial agents febrifugine (d- l) and isofebrifugine (d-2) were synthesized using an unusual Claisen rearrangement of allyl enol ether (7) and the stereoselective reduction of 2- allyl-3-piperidone (8). This method is widely applicable to the synthesis of derivatives needed to study the structure-activity relationship of febrifugine.

Original languageEnglish
Pages (from-to)905-906
Number of pages2
JournalChemical and Pharmaceutical Bulletin
Volume47
Issue number6
DOIs
Publication statusPublished - Jun 1999

Keywords

  • Antimalarial activity
  • Claisen rearrangement
  • Febrifugine
  • Stereoselective reduction
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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