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

19 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

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Keywords

Asymmetric synthesis
Febrifugine
Intramolecular conjugate addition
Lewis acid

ASJC Scopus subject areas

Organic Chemistry
Catalysis

Cite this

Sukemoto, S., Oshige, M., Sato, M., Mimura, K. I., Nishioka, H., Abe, H., Harayama, T., & Takeuchi, Y. (2008). Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition. Synthesis, (19), 3081-3087. [F10608SS]. https://doi.org/10.1055/s-2008-1067271

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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.

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KW - Febrifugine

KW - Intramolecular conjugate addition

KW - Lewis acid

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Access to Document

10.1055/s-2008-1067271