Synthesis of O-aminodihydroartemisinin via TMS triflate catalyzed C-O coupling reaction.
O-Aminodihydroartemisinin was synthesized for the first time via TMS triflate catalyzed coupling reaction of O-acetylartemisinin. The reaction proceeds with high yield without losing the endoperoxide of the artemisinin backbone. The new coupling reaction was employed to prepare artemisinin O-glycosides with improved water solubility. O-Aminodihydroartemisinin reacts readily with benzaldehyde to give the corresponding oxime derivative, demonstrating the potential of this compound for the preparation of various artemisinin conjugates.
Kim
Byung Ju
BJ
Department of Chemistry, University of Washington, Seattle, Washington 98195-1700, USA.
Sasaki
Tomikazu
T
D000588:Amines / Q000737:chemistry*; D037621:Artemisinins / Q000138:chemical synthesis* / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D006031:Glycosylation; D006900:Hydroxylation; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000588:Amines; D037621:Artemisinins; D001547:Benzaldehydes; D008698:Mesylates; D010091:Oximes; D012717:Sesquiterpenes; D014297:Trimethylsilyl Compounds; C039060:artenimol; C012077:trifluoromethanesulfonic acid; C032175:benzaldehyde