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

doi:10.1016/S0040-4020(03)00139-X

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 journal › Article › peer-review

18 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 language	English
Pages (from-to)	1639-1646
Number of pages	8
Journal	Tetrahedron
Volume	59
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4020(03)00139-X
Publication status	Published - Mar 3 2003

Keywords

Antimalarial compounds
Febrifugine
Isomerization
Structural determination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(03)00139-X

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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.",

keywords = "Antimalarial compounds, Febrifugine, Isomerization, Structural determination",

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T1 - Synthesis of febrifugine derivatives and a solution to the puzzle of the structural determination of febrifugine

AU - Takeuchi, Yasuo

AU - Azuma, Kumiko

AU - Oshige, Miyo

AU - Abe, Hitoshi

AU - Nishioka, Hiromi

AU - Sasaki, Kenji

AU - Harayama, Takashi

PY - 2003/3/3

Y1 - 2003/3/3

N2 - 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.

AB - 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.

KW - Antimalarial compounds

KW - Febrifugine

KW - Isomerization

KW - Structural determination

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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