A concise enantioselective synthesis of antimalarial febrifugine alkaloids

H Ooi; A Urushibara; T Esumi; Y Iwabuchi; S Hatakeyama

doi:10.1021/ol015655z

A concise enantioselective synthesis of antimalarial febrifugine alkaloids

Org Lett. 2001 Mar 22;3(6):953-5. doi: 10.1021/ol015655z.

Authors

H Ooi¹, A Urushibara, T Esumi, Y Iwabuchi, S Hatakeyama

Affiliation

¹ Faculty of Pharmaceutical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.

PMID: 11263924
DOI: 10.1021/ol015655z

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis
Alkaloids / chemistry
Antimalarials / chemical synthesis*
Antimalarials / chemistry
Indicators and Reagents
Molecular Conformation
Molecular Structure
Piperidines
Quinazolines / chemical synthesis*
Quinazolines / chemistry
Stereoisomerism

Substances

Alkaloids
Antimalarials
Indicators and Reagents
Piperidines
Quinazolines
febrifugine