Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition

Satoshi Sukemoto; Miyo Oshige; Masahiro Sato; Ken Ichiro Mimura; Hiromi Nishioka; Hitoshi Abe; Takashi Harayama; Yasuo Takeuchi

doi:10.1055/s-2008-1067271

Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition

Satoshi Sukemoto, Miyo Oshige, Masahiro Sato, Ken Ichiro Mimura, Hiromi Nishioka, Hitoshi Abe, Takashi Harayama, Yasuo Takeuchi

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

21 Citations (Scopus)

Abstract

Intramolecular conjugate addition of γ-substituted (E)- α,β-unsaturated ketones with a Lewis acid (BF₃· OEt₂) selectively afforded trans-2,3-disubstituted piperidine derivatives. Chiral substrates were synthesized by Sharpless asymmetric dihydroxylation of the enamine; the antimalarial compound febrifugine was synthesized from the major product of the conjugate addition reaction.

Original language	English
Article number	F10608SS
Pages (from-to)	3081-3087
Number of pages	7
Journal	Synthesis
Issue number	19
DOIs	https://doi.org/10.1055/s-2008-1067271
Publication status	Published - Oct 1 2008

Keywords

Asymmetric synthesis
Febrifugine
Intramolecular conjugate addition
Lewis acid

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-2008-1067271

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Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition. / Sukemoto, Satoshi; Oshige, Miyo; Sato, Masahiro; Mimura, Ken Ichiro; Nishioka, Hiromi; Abe, Hitoshi; Harayama, Takashi; Takeuchi, Yasuo.

In: Synthesis, No. 19, F10608SS, 01.10.2008, p. 3081-3087.

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

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AU - Oshige, Miyo

AU - Sato, Masahiro

AU - Mimura, Ken Ichiro

AU - Nishioka, Hiromi

AU - Abe, Hitoshi

AU - Harayama, Takashi

AU - Takeuchi, Yasuo

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N2 - Intramolecular conjugate addition of γ-substituted (E)- α,β-unsaturated ketones with a Lewis acid (BF3· OEt2) selectively afforded trans-2,3-disubstituted piperidine derivatives. Chiral substrates were synthesized by Sharpless asymmetric dihydroxylation of the enamine; the antimalarial compound febrifugine was synthesized from the major product of the conjugate addition reaction.

AB - Intramolecular conjugate addition of γ-substituted (E)- α,β-unsaturated ketones with a Lewis acid (BF3· OEt2) selectively afforded trans-2,3-disubstituted piperidine derivatives. Chiral substrates were synthesized by Sharpless asymmetric dihydroxylation of the enamine; the antimalarial compound febrifugine was synthesized from the major product of the conjugate addition reaction.

KW - Asymmetric synthesis

KW - Febrifugine

KW - Intramolecular conjugate addition

KW - Lewis acid

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Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition

Abstract

Keywords

ASJC Scopus subject areas

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