A concise enantioselective synthesis of antimalarial febrifugine alkaloids

Hidenori Ooi; Ayumi Urushibara; Tomoyuki Esumi; Yoshiharu Iwabuchi; Susumi Hatakeyama

doi:10.1021/ol015655z

A concise enantioselective synthesis of antimalarial febrifugine alkaloids

Hidenori Ooi, Ayumi Urushibara, Tomoyuki Esumi, Yoshiharu Iwabuchi, Susumi Hatakeyama

PHA - Molecular Pharmaceutical Science

Nagasaki University

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

85 Citations (Scopus)

Abstract

matrix presented Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.

Original language	English
Pages (from-to)	953-955
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	6
DOIs	https://doi.org/10.1021/ol015655z
Publication status	Published - 2001 Mar 22

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10.1021/ol015655z

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abstract = "matrix presented Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.",

author = "Hidenori Ooi and Ayumi Urushibara and Tomoyuki Esumi and Yoshiharu Iwabuchi and Susumi Hatakeyama",

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T1 - A concise enantioselective synthesis of antimalarial febrifugine alkaloids

AU - Ooi, Hidenori

AU - Urushibara, Ayumi

AU - Esumi, Tomoyuki

AU - Iwabuchi, Yoshiharu

AU - Hatakeyama, Susumi

PY - 2001/3/22

Y1 - 2001/3/22

N2 - matrix presented Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.

AB - matrix presented Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.

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JO - Organic Letters

JF - Organic Letters

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ER -

A concise enantioselective synthesis of antimalarial febrifugine alkaloids

Abstract

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