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
Publication statusPublished - 1999

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Piperidones
Antimalarials
Structure-Activity Relationship
Ether
Derivatives
febrifugine

Keywords

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

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Total synthesis of dl-febrifugine and dl-isofebrifugine. / Takeuchi, Yasuo; Abe, Hitoshi; Harayama, Takashi.

In: Chemical and Pharmaceutical Bulletin, Vol. 47, No. 6, 1999, p. 905-906.

Research output: Contribution to journalArticle

Takeuchi, Yasuo ; Abe, Hitoshi ; Harayama, Takashi. / Total synthesis of dl-febrifugine and dl-isofebrifugine. In: Chemical and Pharmaceutical Bulletin. 1999 ; Vol. 47, No. 6. pp. 905-906.
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