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    Evaluation and optimization of synthetic routes from dihydroartemisinin to the alkylamino-artemisinins artemiside and artemisone: a test of N-glycosylation methodologies on a lipophilic peroxide

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    Date
    2018
    Author
    Chan, Wing Chi
    Haynes, Richard K.
    Wai Chan, Dennis Ho
    Lee, Kin Wo
    Tin, Wing Shan
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    Abstract
    10-Alkylamino-artemisinins including artemiside and artemisone display enhanced activities against malaria. Earlier, dihydroartemisinin (DHA) TMS ether was converted by trimethylsilyl bromide into the 10-β-bromide that with amine nucleophiles provided the amino-artemisinins. In an attempt to develop more economic approaches, direct N-glycosylation of DHA was examined but 2-deoxyartemisinin was invariably obtained. However, hydroxyl group activation by conversion into the 10β-halide in non-polar solvents with anhydrous HCl and Group I and II metal halides, oxalyl chloride or thionyl chloride with catalytic DMSO, and oxalyl bromide did succeed. The β-halides were converted in situ by thiomorpholine into artemiside, and by thiomorpholine-1,1-dioxide into artemisone respectively in scalable reactions. Hydrogen peroxide-acetonitrile or the urea-hydrogen peroxide complex efficiently oxidized the sulfide artemiside to the sulfone artemisone. Overall, a generalized approach to 10-alkylamino-artemisinins is now available
    URI
    http://hdl.handle.net/10394/26849
    https://doi.org/10.1016/j.tet.2018.04.027
    https://www.sciencedirect.com/science/article/pii/S004040201830406X
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