Acid catalyzed Michael additions to artemisitene.
A series of 14-substituted-artemisinin and 9-epiartemisinin derivatives was prepared by a titanium-tetrachloride catalyzed addition of trimethylsilyl enol ethers to artemisitene. Several compounds were four to seven times more active than artemisinin against Plasmodium falciparum.
Laboratory of Bioorganic Chemistry, NIDDK, Bethesda, MD 20892, USA.
J
J
Ma
E
E
Weiss
D E
DE
Kyle
H
H
Ziffer
D037621:Artemisinins; D002384:Catalysis; D004987:Ethers; D007202:Indicators and Reagents; D007700:Kinetics; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014025:Titanium
D037621:Artemisinins; D004987:Ethers; D007202:Indicators and Reagents; D012717:Sesquiterpenes; C105118:artemisitene; C025096:titanium tetrachloride; D014025:Titanium