Synthesis of febrifugine derivatives and a solution to the puzzle of the structural determination of febrifugine

Yasuo Takeuchi, Kumiko Azuma, Miyo Oshige, Hitoshi Abe, Hiromi Nishioka, Kenji Sasaki, Takashi Harayama

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The stereo-structure of piperidine lactone (3), a synthetic intermediate of the antimalarial agent febrifugine ((+)-1) with a piperidine ring in the trans relative configuration, was re-revised to the cis-form. We determined that isomerization to the trans-form from the cis-form occurred in the stage (6 from 5) of deprotection in Baker's synthesis.

Original languageEnglish
Pages (from-to)1639-1646
Number of pages8
JournalTetrahedron
Volume59
Issue number10
DOIs
Publication statusPublished - Mar 3 2003

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Antimalarials
Isomerization
Derivatives
piperidine
piperidine lactone
febrifugine

Keywords

  • Antimalarial compounds
  • Febrifugine
  • Isomerization
  • Structural determination

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of febrifugine derivatives and a solution to the puzzle of the structural determination of febrifugine. / Takeuchi, Yasuo; Azuma, Kumiko; Oshige, Miyo; Abe, Hitoshi; Nishioka, Hiromi; Sasaki, Kenji; Harayama, Takashi.

In: Tetrahedron, Vol. 59, No. 10, 03.03.2003, p. 1639-1646.

Research output: Contribution to journalArticle

Takeuchi, Yasuo ; Azuma, Kumiko ; Oshige, Miyo ; Abe, Hitoshi ; Nishioka, Hiromi ; Sasaki, Kenji ; Harayama, Takashi. / Synthesis of febrifugine derivatives and a solution to the puzzle of the structural determination of febrifugine. In: Tetrahedron. 2003 ; Vol. 59, No. 10. pp. 1639-1646.
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