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  • Synthetic Investigation tow...
    Ge, Shi‐Jie; Tu, Yuan‐Hong; Xia, Jian‐Hui; Sun, Jian‐Song

    European journal of organic chemistry, July 25, 2017, Volume: 2017, Issue: 27
    Journal Article

    Leveraging on the orchestrated application of both Schmidt and Yu glycosylations, the first total syntheses of the echinocystic acid saponins pithedulosides D and E, the two antitumoral and representative D‐ring‐functionalized oleanane‐type saponins, were achieved. Benefitting from the applied convergent synthetic strategy, the echinocystic acids could be synthesized in overall yields of as high as 71 and 76 % through four linear steps. The first total syntheses of the bioactive echinocystic acid saponins pithedulosides D and E are achieved by a convergent strategy using glycoysyl trichloroacetimidate and a glycosyl ortho‐alkynylbenzoate as donors.