Reaction Steps
A solution of 3-benzyloxy-2-ethyl-17-(2-methoxy-ethylidene)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene (0.43 g, 1 mmol) in 50 ml tert-butanol was reflux and Na (0.46 g, 20 mmol) was added in small portions over a period of 6 hours. The mixture was refluxed for 18 h, cooled to room temperature and 2-propanol added to destroy excess sodium. The solvents were evaporated and the residual solid poured in water (20 ml). The organics were extracted with ethyl acetate and the organic layer was washed with water, brine, dried over MgSO4. The solvent was evaporated under vacuum. The crude oil was purified by chromatography (hexane/ethylacetate 15/1 to 8:1) to give 2-ethyl-17-(2-methoxy-ethylidene)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-ol as a white powder, 230 mg (68%), mp=133-134° C.; 1H NMR (CDCl3, 270 MHz): 0.79 (s, 3H, CH3), 1.22 (t, J=7.4 Hz, 3H, CH3), 1.28-1.60 (m, 6H), 1.75-1.96 (m, 3H), 2.18 (m, 1H), 2.39 (m, 3H), 2.59 (q, J=7.4 Hz, 2H, CH2), 2.79 (m, 2H, H6), 3.35 (s, 3H, CH3O), 3.94 (m, 2H, CH2OMe), 5.11 (s, 1H, OH), 5.24 (m, 1H, CHCH2OH), 6.48 (s, 1H, ArH), 7.05 (s, 1H, ArH). 13C NMR (CDCl3, 400 MHz): 14.9 (CH3), 19.2, 23.5, 24.4, 26.7, 27.1, 28.1, 29.7, 36.4, 39.1, 44.4, 44.8, 53.5, 58.2, 70.2, 112.8, 115.7, 126.4, 127.5, 132.6, 135.5, 151.5, and 157.1. HPLC: 98%; HRMS (FAB+): found 340.24023 calcd. C23H32O2 340.24023.
