Synthesis of O-aminodihydroartemisinin via TMS triflate catalyzed C-O coupling reaction
Synthesis of O-aminodihydroartemisinin via TMS triflate catalyzed C-O coupling reaction
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DOI：
10.1021/jo0498765
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发表时间：
2004-04-30
影响因子：
3.6
通讯作者：
Sasaki, T
中科院分区：
文献类型：
--
作者：
Kim, BJ;Sasaki, T
采用三氟化三甲醚催化o -乙酰青蒿素偶联反应，首次合成了o -氨基二氢青蒿素。该反应在不损失青蒿素主链内过氧化物的情况下以高收率进行。利用新的偶联反应制备了水溶性较好的青蒿素o -糖苷。邻氨基二氢青蒿素很容易与苯甲醛反应生成相应的肟衍生物，表明该化合物具有制备各种青蒿素偶联物的潜力。
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.