title: Synthesis of O-aminodihydroartemisinin via TMS triflate catalyzed C-O coupling reaction.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Washington, Seattle, Washington 98195-1700, USA.
authors.forename: Byung Ju
authors.initials: BJ
authors.lastname: Kim
authors.forename: Tomikazu
authors.initials: T
authors.lastname: Sasaki
mesh_terms: 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*
chemical_list: D000588:Amines; D037621:Artemisinins; D001547:Benzaldehydes; D008698:Mesylates; D010091:Oximes; D012717:Sesquiterpenes; D014297:Trimethylsilyl Compounds; C039060:artenimol; C012077:trifluoromethanesulfonic acid; C032175:benzaldehyde