Reaction SMILES: [Cl-].[Ce+3].[Cl-].[Cl-].[C:5]1([Mg]Br)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:13]([C@@:20]12[CH2:33]/[C:32](=[CH:34]\[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)/[C:31](=[O:41])[CH2:30][C@H:29]1[CH2:28][CH2:27][C:26]1[CH:25]=[C:24]([C:42]([OH:44])=[O:43])[CH:23]=[CH:22][C:21]2=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([Mg]Br)C1C=CC=CC=1>O1CCCC1.O.CO>[CH2:13]([C@@:20]12[CH2:33]/[C:32](=[CH:34]\[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)/[C@:31]([OH:41])([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:30][C@H:29]1[CH2:28][CH2:27][C:26]1[CH:25]=[C:24]([C:42]([OH:44])=[O:43])[CH:23]=[CH:22][C:21]2=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
Reactant: O=C1C[C@H]2CCc3cc(C(=O)O)ccc3[C@]2(Cc2ccccc2)C/C1=C\c1ccccc1
Reactant: Br[Mg]c1ccccc1
Agent: Br[Mg]Cc1ccccc1
Agent: [Ce+3]
Agent: [Cl-]
Solvent: C1CCOC1
Solvent: O
Solvent: CO
Product: O=C(O)c1ccc2c(c1)CC[C@@H]1C[C@@](O)(c3ccccc3)/C(=C/c3ccccc3)C[C@@]21Cc1ccccc1
Temperature: 10 °C
Reaction time: 0.25 h
Yield: 81.7 %

Procedure:
Cerium (III) Chloride (5.00 g, 20.29 mmol) was mixed in tetrahydrofuran (50 mL) at 50° C. for 16 hours. The temperature of the reaction was internally monitored with a JKEM. The resulting white milky solution was cooled to −75 C and stirred vigorously. The cold slurry was charged with phenyl magnesium bromide (1.0 M in THF, 19.1 mmol) dropwise over 15 minutes with the temperature maintained below −70° C. The solution was kept at −73° C. for 15 minutes and a solution of (4bR,6E,8aR)-4b-benzyl-6-benzylidene-7-oxo-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-2-carboxylic acid (3.5 g, 8.311 mmol) in tetrahydrofuran (40 mL) was added dropwise over 20 minutes maintaining the reaction temperature below −70° C. HPLC/MS was obtained and indicated remaining starting material. The reaction was mixed for an additional 3 hours and an HPLC/MS was obtained and starting material remained. An additional 2 mL of benzyl magnesium bromide solution (2.0 mmol) was added over 10 minutes and an HPLC/MS obtained. An additional 1 mL of benzyl magnesium bromide solution (1.0 mmol) was added over 10 minutes and an HPLC/MS obtained. The solution was mixed for 30 minutes at −73° C. and allowed to warm to 10° C. and then cooled to 0° C. The reaction was quenched by the addition of saturated aqueous KHSO4 dropwise maintaining the temperature below 10° C. A total of 50 ml of the saturated solution was added. Solids formed in the solution and were removed by vacuum filtratration. The filter cake was washed with tetrahydrofuran (40 mL) and water (40 mL). Ethyl acetate (100 mL) was added and the layers separated. The organic layer was washed with saturated ammonium chloride (100 mL), dried over sodium sulfate, and solvent removed at reduced pressure. The aqueous layer was checked by HPLC/MS and did not contain any product. The residue was taken up in methanol (15 ml) and water added. The solution became milky and eventually a precipitate formed. Small amounts of methanol and water were added to improve the quality and quantity of precipitate. The solids were collected by vacuum filtration and air dried for about 2 hours. 3.4 grams of the title compound as a light yellow solid was obtained in 81% yield. 1H NMR (400 MHz, DMSO-d6) d ppm 12.65 (1H, s), 7.44-7.56 (7H, m), 7.34-7.39 (2H, m), 7.30 (2H, t, J=7.7 Hz), 7.12-7.22 (2H, m), 6.78 (1H, t, J=7.4 Hz), 6.50 (2H, t, J=7.8 Hz), 6.12 (1H, d, J=8.3 Hz), 5.86 (2H, d, J=7.3 Hz), 5.44 (1H, s), 3.61 (1H, d, J=14.2 Hz), 2.96 (1H, dd, J=17.6, 7.9 Hz), 2.80-2.91 (1H, m), 2.66-2.74 (1H, m), 2.50-2.65 (2H, m), 2.08 (1H, t, J=13.3 Hz), 1.82-1.93 (1H, m, J=13.2 Hz), 1.75-1.82 (1H, m), 1.59-1.74 (2H, m); LC/MS, tr=3.77 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min, at 254 nm, at 50° C.).