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. 2018 Nov 13;9(12):1269–1273. doi: 10.1021/acsmedchemlett.8b00442

Scheme 1. Synthesis of 12-Thiazole Abietanes 58 and 1114 from Dehydroabietic Acid 1.

Scheme 1

Reagents and conditions: (a) MeI, K2CO3, DMF, rt, 2.5 h; (b) MeCOCl, AlCl3, CH2Cl2, 0 °C → rt, 3.5 h; (c) CuBr2, MeOH, 65 °C, 16 h; (d) thiourea, Et3N, dry EtOH, reflux, 1 h 45 min, or 120 °C with microwaves, 30 min; (e) thioformamide, dry 1,4-dioxane, 100 °C with microwaves, 10 min; (f) LiAlH4, THF, 0 °C → rt; (g) KOH, ethylene glycol, H2O, 130 °C; (h) HOBt, EDC-HCl, aq NH3, DMF, 0 °C → rt, 19 h.