Synthesis of antimalarial 1,2,4-trioxanes via photooxygenation of a chiral allylic alcohol.
[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.
Griesbeck
Axel G
AG
Institute of Organic Chemistry, University of Cologne, Greinstr. 4, D-50939 Köln, Germany. griesbeck@uni-koeln.de
El-Idreesy
Tamer T
TT
Fiege
Maren
M
Brun
Reto
R
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010963:Plasmodium falciparum / Q000187:drug effects
D000962:Antimalarials