An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity.
Here we present an efficient route into synthetically challenging bridged 1,2,4,5-tetraoxanes. The key to the success of this route is the use of H(2)O(2) and catalytic I(2) to form the gem-dihydroperoxide followed by a Ag(2)O mediated alkylation using 1,3-diiodopropane. Using this methodology a range of bridged tetraoxanes which display good in vitro antimalarial activity were synthesized.
Ellis
Gemma L
GL
Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK.
Amewu
Richard
R
Hall
Charlotte
C
Rimmer
Karen
K
Ward
Steven A
SA
O'Neill
Paul M
PM
D000818:Animals; D000962:Antimalarials / Q000737:chemistry* / Q000494:pharmacology*; D000077549:Artemether; D037621:Artemisinins / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects; D013329:Structure-Activity Relationship; D045568:Tetraoxanes / Q000737:chemistry* / Q000494:pharmacology*
D000962:Antimalarials; D037621:Artemisinins; D045568:Tetraoxanes; C031327:artemisinin; D000077549:Artemether