Total synthesis of dl-febrifugine and dl-isofebrifugine

Yasuo Takeuchi; Hitoshi Abe; Takashi Harayama

doi:10.1248/cpb.47.905

Total synthesis of dl-febrifugine and dl-isofebrifugine

Yasuo Takeuchi, Hitoshi Abe, Takashi Harayama

Research output: Contribution to journal › Article › peer-review

33 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 language	English
Pages (from-to)	905-906
Number of pages	2
Journal	Chemical and Pharmaceutical Bulletin
Volume	47
Issue number	6
DOIs	https://doi.org/10.1248/cpb.47.905
Publication status	Published - Jun 1999

Keywords

Antimalarial activity
Claisen rearrangement
Febrifugine
Stereoselective reduction
Total synthesis

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.47.905

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author = "Yasuo Takeuchi and Hitoshi Abe and Takashi Harayama",

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AU - Abe, Hitoshi

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AB - 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.

KW - Antimalarial activity

KW - Claisen rearrangement

KW - Febrifugine

KW - Stereoselective reduction

KW - Total synthesis

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Total synthesis of dl-febrifugine and dl-isofebrifugine

Abstract

Keywords

ASJC Scopus subject areas

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