Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 00 Praha 2, Czech Republic.
Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 00 Praha 2, Czech Republic.
Org Biomol Chem. 2021 Apr 26;19(15):3434-3440. doi: 10.1039/d1ob00205h.
A method for the synthesis of fused 1,2-naphthoquinones, as analogues of biologically active natural terpene quinones, is described. The intermediate polycyclic naphthalenes were prepared by a one-pot palladium-catalysed process from simple alkynes, one of which was made from an optically pure biomass-derived levoglucosenone. The prepared methoxy-substituted naphthalenes were subsequently transformed in one step to 1,2-naphthoquinones by a trivalent-iodine-mediated oxidation. The naphthoquinone products were found to have cytotoxic properties.
描述了一种合成稠合 1,2-萘醌类化合物的方法，此类化合物是具有生物活性的天然萜烯醌类化合物的类似物。通过一锅法钯催化过程，从简单的炔烃（其中一个炔烃由光学纯的生物质衍生的左旋葡庚酮制成）制备了中间多环萘。随后，通过三价碘介导的氧化，将制备的甲氧基取代的萘一步转化为 1,2-萘醌。发现萘醌产物具有细胞毒性。
