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. 2024 Apr 24;89(9):6444–6455. doi: 10.1021/acs.joc.4c00440

Scheme 5. Synthesis of Isocanthin-4-one 10a.

Scheme 5

Reagents and conditions: (i) Meldrum’s acid (1.1 equiv), CH(OEt)3 (1.2 equiv), MeCN, ∼82 °C, 5 h, 75%; (ii) Ph2O, ∼250 °C, 0.5 min, 85%; (iii) 2-ClC6H4B(OH)2 (1.5 equiv), Pd(dppf)Cl2·DCM (5 mol %), K2CO3 (2 equiv), dioxane/H2O (75:25), ∼88 °C, 15 min; (iv) K2CO3 (2 equiv), CuI (10 mol %), DMCDA (20 mol %), H2O (1 equiv), dioxane/H2O (75:25), ∼88 °C, 12 h, 77%.