“…The combined extracts were washed with brine and dried. Solvent removal, chromatography (20% EtOAc in hexanes) and recrystallization from acetone/hexanes gave product 17a (30 70 (s, 3H, C 18 -CH 3 ), 2.77-2.78 (m, 2H, C 6 -CH 2 ), 3.75 (q, J = 6 Hz, 1H, C 17 -H), 6.54 (d, 1H, J = 2.4 Hz, C 4 -H), 6.59 (dd, 1H, J = 8.4 Hz, 2.4 Hz, C 2 -H), 7.10 (d, 1H, J = 8.4 Hz, C 1 -H); 13 24. (8α,13α,14β,17β)-Estra-1,3,5(10),9(11)-tetraene-3,17-diol (17b)-A solution of compound 16b (60 mg, 0.21 mmol) in anhydrous toluene (3 ml) under N 2 was added to DIBALH (1.5 M in toluene, 1.5 ml, 2.25 mmol).…”