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. 2020 Mar 5;11(5):798–805. doi: 10.1021/acsmedchemlett.9b00617

Scheme 1. Synthetic Route to 6ah and 7ah Derivatives.

Scheme 1

Reagents and conditions: (i) TosMIC, NaH, 2:1 Et2O dry/DMSO dry, N2, room temp, 1 h, 100% yield; (ii) proper arylalkyl halide, DMF, K2CO3, 80 °C, overnight, 55–70% yield; (iii) diethyl oxalate, EtONa, THF dry, N2, room temperature, 2 h, 97–100% yield; (iv) MeOH, NH2NH2 dihydrochloride, Et3N, CH3COOH gl, room temperature, 2 h, 60–100% yield; (v) THF, NaOH 20%, 90 or 100 °C, 6–12 h, 65–98% yield.