Reaction SMILES: [CH2:1]([C@@:8]12[CH2:21][C@:20]([OH:23])([CH3:22])[C@:19]([OH:30])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][C@H:17]1[CH2:16][CH2:15][C:14]1[CH:13]=[C:12]([C:31]([NH:33][C:34]3[C:35]([CH3:40])=[N:36][CH:37]=[CH:38][CH:39]=3)=[O:32])[CH:11]=[CH:10][C:9]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[O:42]=[O+][O-].O=O>C(Cl)Cl.CO>[CH2:1]([C@@:8]12[CH2:21][C@:20]([OH:23])([CH3:22])[C@:19]([OH:30])([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:18][C@H:17]1[CH2:16][C:15](=[O:42])[C:14]1[CH:13]=[C:12]([C:31]([NH:33][C:34]3[C:35]([CH3:40])=[N:36][CH:37]=[CH:38][CH:39]=3)=[O:32])[CH:11]=[CH:10][C:9]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: O=[O+][O-]
Reactant: Cc1ncccc1NC(=O)c1ccc2c(c1)CC[C@@H]1C[C@@](O)(c3ccccc3)[C@](C)(O)C[C@@]21Cc1ccccc1
Agent: Cl
Agent: O=O
Solvent: ClCCl
Solvent: CO
Product: Cc1ncccc1NC(=O)c1ccc2c(c1)C(=O)C[C@@H]1C[C@@](O)(c3ccccc3)[C@](C)(O)C[C@@]21Cc1ccccc1
Temperature: -78 °C
Reaction time: 0.17 h

Procedure:
A sample of solid (4bR,6R,7R,8aR)-4b-benzyl-6,7-dihydroxy-6-methyl-N-(2-methylpyridin-3-yl)-7-phenyl-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-2-carboxamide (2200 mg, 4.130 mmol) was dissolved at room temperature solution in methylene chloride (10 mL) and methanol (100 mL). This resulting solution was treated with a 10 mL solution of 2 N HCl in MeOH and was stirred for an additional 10 minutes. The reaction solution was visually inspected at this time to ensure that all solids were dissolved and then was cooled to −78° C. The cooled solution was treated with a steady stream of ozone (5 cc flow rate, generated using a Azcozon generator, AZCO Industries Ltd., model #RMU16-8 with O2 pressure set to 30 psi). After five hours of constant ozone flow, the reaction was nearly complete to desired title compound by LCMS analysis (M+H LRMS 547.2 amu). The solution had taken on a deep blue color. The cold reaction solution was flushed with nitrogen for 5 minutes to dissipate most of the ozone and the reaction took on a significantly less blue color. At this time, 20 mL of dimethyl sulfide was added in a manner that did not raise the internal reaction temperature above −70 C. This was followed by removal of the cooling bath and the reaction was allowed to warm on its own accord to room temperature (1 hour), and was maintained at this temperature for 3 hours additional. At this time, the reaction solution was concentrated to a residue and dissolved in 25 mL of THF, and then the resulting THF solution was directly subjected to C-18 reverse phase chromatography (15 minute gradient run, 5% acetonitrile mobile phase to 95% acetonitrile mobile phase and water). The resulting title compound was filtered through an exchange resin (StratoSphere SPE, PL-HCO3 MP-Resin, product number 3540-C603) to remove any TFA salts and provide the title product as its parent compound. The resulting solid was crystallized by the following procedure: The solid was slurried with MeOH (7 mL), the solids collected after 1 hour and washed with an additional 2 mL of MeOH to furnish the title compound 1802 mg, 79%. Analytical data as follows: 1H NMR (500 MHz, D6 DMSO) δ ppm 1.18 (s, 3 H) 1.51 (dd, J=12.66, 1.96 Hz, 1 H) 1.99 (d, J=14.96 Hz, 1 H) 2.40 (dd, J=18.88, 4.85 Hz, 1 H) 2.43-2.49 (m, 1 H) 2.49 (br. s., 3 H) 2.56 (t, J=12.82 Hz, 1 H) 2.61 (d, J=12.53 Hz, 1 H) 2.75 (d, J=15.12 Hz, 1 H) 2.92 (dd, J=18.59, 12.74 Hz, 1 H) 4.05 (d, J=12.45 Hz, 1 H) 6.65 (d, J=8.27 Hz, 1 H) 6.79 (dd, J=7.69, 1.59 Hz, 2 H) 7.05-7.13 (m, 3 H) 7.15-7.21 (m, 1 H) 7.25 (t, J=7.69 Hz, 2 H) 7.49 (dd, J=7.94, 5.10 Hz, 1 H) 7.62 (dd, J=7.44, 1.25 Hz, 2 H) 7.87 (dd, J=8.23, 2.13 Hz, 1 H) 8.01 (dd, J=7.78, 1.00 Hz, 1 H) 8.46 (dd, J=5.01, 1.50 Hz, 1 H) 8.54 (d, J=2.09 Hz, 1 H) 10.18-10.58 (m, 1 H, NH). Dependant upon the water content of DMSO, two OH protons can be visible at 4.78 and 5.44 ppm. HRMS m/z 547.2619 (C35H35N2O4: calcd for M+H, 547.2591).