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

22 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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title = "Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition",

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.",

keywords = "Asymmetric synthesis, Febrifugine, Intramolecular conjugate addition, Lewis acid",

author = "Satoshi Sukemoto and Miyo Oshige and Masahiro Sato and Mimura, {Ken Ichiro} and Hiromi Nishioka and Hitoshi Abe and Takashi Harayama and Yasuo Takeuchi",

year = "2008",

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doi = "10.1055/s-2008-1067271",

language = "English",

pages = "3081--3087",

journal = "Synthesis",

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T1 - Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition

AU - Sukemoto, Satoshi

AU - Oshige, Miyo

AU - Sato, Masahiro

AU - Mimura, Ken Ichiro

AU - Nishioka, Hiromi

AU - Abe, Hitoshi

AU - Harayama, Takashi

AU - Takeuchi, Yasuo

PY - 2008/10/1

Y1 - 2008/10/1

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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DO - 10.1055/s-2008-1067271

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EP - 3087

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 19

M1 - F10608SS

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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