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Synthesis of d-secoestrone derivatives (12a–e and 13a–e). Reagents and conditions: (i) 5 equiv. KBH4, CH2Cl2:MeOH = 1:1, 0 °C—r.t., 0.5 h; (ii) H2 (20 bar), Pd/C, EtOAc, 3 h; (iii) propargyl bromide (1.5 equiv.), K2CO3 (7 equiv.), acetone, 70 °C, 24 h; (iv) CuI (0.05 equiv.), Ph3P (0.1 equiv.), DIPEA (3 equiv.), toluene, reflux, 2 h.
