School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China.
J Org Chem. 2023 May 5;88(9):5348-5358. doi: 10.1021/acs.joc.2c02898. Epub 2023 Apr 3.
A facile access to isocoumarins has been established rhodium(III)-catalyzed C-H bond activation and intramolecular C-C cascade annulation of enaminones and cyclic 1,3-dicarbonyl compounds. The synthetic protocol features a wide range of substrates with high functional group tolerance, mild reaction conditions, and the selective cleavage of the enaminone C-C bond. Notably, the cyclic 1,3-dicarbonyl compounds can -generate iodonium ylide as a carbene precursor to prepare polycyclic scaffolds by reacting with PhI(OAc). The application of this method to prepare useful synthetic precursors and bioactive skeletons is also exemplified.
建立了一种简便的异香豆素合成方法，即通过铑(III)催化的烯胺酮和环状 1,3-二羰基化合物的 C-H 键活化和分子内 C-C 级联环化反应。该合成方案具有广泛的底物适用性、高官能团容忍度、温和的反应条件以及对烯胺酮 C-C 键的选择性断裂等特点。值得注意的是，环状 1,3-二羰基化合物可以生成碘𬭩叶立德作为卡宾前体，与 PhI(OAc)反应制备多环支架。该方法在制备有用的合成前体和生物活性骨架方面的应用也得到了例证。
