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.
Ma
J
J
Laboratory of Bioorganic Chemistry, NIDDK, Bethesda, MD 20892, USA.
Weiss
E
E
Kyle
D E
DE
Ziffer
H
H
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