Scheme 2.
Synthesis of diosgenin–benzoic acid mustard hybrids 14a−14f and 15a−15f. Reagents and conditions: (a) Jones reagent, THF/acetone (1/1), rt, 3 h; (b) N-Boc-protected amines, TBTU, DIPEA, CH2Cl2, rt, 8 h; (c) CF3COOH, CH2Cl2, rt, 4 h; (d) Benzoic acid mustard, DMAP, EDCI, CH2Cl2, rt, 24 h; (e) NaOH, CH3OH/THF (1/1.5), rt, 6 h.