Reaction SMILES: FC(S(O[C:9]1[C:26]([O:27][CH3:28])=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[CH2:29])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)(=O)=O)(F)F.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Si](C)(C)N[Si](C)(C)C.C[N:69](C)[CH:70]=[O:71]>[Pd](Cl)Cl>[CH3:28][O:27][C:26]1[C:9]([C:70]([NH2:69])=[O:71])=[CH:10][C:11]2[CH2:12][CH2:13][C@@H:14]3[C@@H:23]([C:24]=2[CH:25]=1)[CH2:22][CH2:21][C@@:19]1([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]1=[CH2:29]
Reactant: C=C1CC[C@H]2[C@@H]3CCc4cc(OS(=O)(=O)C(F)(F)F)c(OC)cc4[C@H]3CC[C@]12C
Reactant: CN(C)C=O
Agent: Cl[Pd]Cl
Agent: C[Si](C)(C)N[Si](C)(C)C
Agent: c1ccc(P(CCCP(c2ccccc2)c2ccccc2)c2ccccc2)cc1
Product: C=C1CC[C@H]2[C@@H]3CCc4cc(C(N)=O)c(OC)cc4[C@H]3CC[C@]12C
Temperature: 100 °C
Reaction time: 18 h

Procedure:
A 250 mL three-necked flask equipped with an overhead stirrer, thermocouple, and nitrogen inlet, was charged with 2-Methoxy-17-methyleneestra-1,3,5(110)-trien-3-yl(trifluoromethyl)-sulfonate (Scheme 5, Compound 48) (20.0 g, 46.5 mmol), palladium (II) chloride (0.41 g, 2.3 mmol), 1,3-bis(diphenylphosphino)propane (1.9 g, 4.6 mmol), 1,1,1,3,3,3-hexamethyldisilazane (38.8 mL, 186 mmol) and anhydrous dimethylformamide (150 mL). The resulting orange solution was evacuated and back-filled with nitrogen three times, then evacuated and back-filled with carbon monoxide three times. The reaction was warmed to 100° C. and stirred under a carbon monoxide atmosphere (balloon) for 18 hours, during which time the solution became dark red. The heat was removed, methanol (40 mL) was added, and stirred for 10 minutes. The solution was poured into ethyl acetate (1 L) and extracted with 2 N H2SO4 (1 L). The aqueous layer was extracted with ethyl acetate (3×500 ml). Each of the ethyl acetate extracts was washed with 2 N H2SO4 (500 mL). The combined organic phases were washed with saturated aqueous sodium bicarbonate (1 L) and dried over sodium sulfate (500 g). This suspension was suction-filtered through a bed of silica gel 60 (102 g), and the filtrate concentrated to dryness affording 16.02 g (106% recovery) of crude (Scheme 5, Compound 60). The crude product was purified on silica gel 60 (500 g, flash column) eluting with methylene chloride (2 L) then 2% methanol-methylene chloride (4 L) then 4% methanol-methylene chloride (4 L). Chromatography failed to remove all impurities so fractions containing product were combined, concentrated to dryness, and repurified on silica gel 60 (500 g, flash column) eluting with methylene chloride (2 L) then 1:5 ethyl acetate-methylene chloride. Concentration of the pure fractions (TLC, 1:5 ethyl acetate-methylene chloride, Rf=0.3, UV detection) and drying in a vacuum oven at 80° C., afforded 12.3 g (81% overall) of (Scheme 5, Compound 60) as a light-yellow solid. Removal of methylene chloride yielded 11.36 g of (Scheme 5, Compound 60) (75% overall yield) as a light-yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.94 (s, 1H), 7.63 (br s, 1H), 6.95 (s, 1H), 5.70 (br s, 1H), 4.71 (s, 2H), 3.97 (s, 3H), 2.97-2.82 (m, 2H), 2.65-1.19 (m, 13H), 0.86 (s, 3H). 13C NMR (CDCl3, 125 MHz) δ 167.2, 161.4, 155.8, 146.3, 132.6, 129.6, 118.0, 108.4, 100.9, 55.9, 53.5, 44.9, 44.2, 38.2, 35.6, 29.4, 28.4, 27.4, 26.4, 23.9, 18.5.