Synthesis of antimalarial 1,2,4-trioxanes via photooxygenation of a chiral allylic alcohol

Axel G Griesbeck; Tamer T El-Idreesy; Maren Fiege; Reto Brun

doi:10.1021/ol026916n

Synthesis of antimalarial 1,2,4-trioxanes via photooxygenation of a chiral allylic alcohol

Org Lett. 2002 Nov 28;4(24):4193-5. doi: 10.1021/ol026916n.

Authors

Axel G Griesbeck¹, Tamer T El-Idreesy, Maren Fiege, Reto Brun

Affiliation

¹ Institute of Organic Chemistry, University of Cologne, Greinstr. 4, D-50939 Köln, Germany. griesbeck@uni-koeln.de

PMID: 12443056
DOI: 10.1021/ol026916n

Abstract

[reaction: see text] Photooxygenation of the chiral allylic alcohol 4-methyl-3-penten-2-ol (3) in nonpolar solvents and subsequent Lewis acid-catalyzed peroxyacetalization afforded a series of monocyclic and spirobicyclic 1,2,4-trioxanes (5, 6). Two products show significant anti-Malaria activity against Plasmodium falciparum when compared with chloroquine.

Publication types

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

MeSH terms

Animals
Antimalarials / chemical synthesis*
Antimalarials / chemistry*
Antimalarials / pharmacology
Drug Design
Magnetic Resonance Spectroscopy
Molecular Structure
Oxidation-Reduction
Plasmodium falciparum / drug effects

Substances

Antimalarials