[NH:1]1CCC[C@H]1C(O)=O.[OH-:9].[Na+].Br[C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[CH2:19][C:20]2([C:25]3[CH:26]=[CH:27][C:28](=[O:32])[N:29]([CH3:31])[N:30]=3)OCCO2)=[CH:14][CH:13]=1.[CH3:40][S:41]([O-:43])=[O:42].[Na+]>[Cu]I.CS(C)=O>[OH:9]/[N:1]=[C:20](/[C:25]1[CH:26]=[CH:27][C:28](=[O:32])[N:29]([CH3:31])[N:30]=1)\[CH2:19][C@H:18]([C:15]1[CH:16]=[CH:17][C:12]([S:41]([CH3:40])(=[O:43])=[O:42])=[CH:13][CH:14]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39]L-proline (7.5 mg, 65 μmol) was combined with dimethyl sulfoxide (1 ml), then sodium hydroxide (2.6 mg, 65 μmol) was added and the reaction stirred at room temperature for 30 min, then (R)-6-(2-(2-(4-bromophenyl)-2-o-tolylethyl)-1,3-dioxolan-2-yl)-2-methylpyridazin-3(2H)-one (37 mg, 81 μmol), sodium methanesulfinate (68 mg, 650 μmol) and copper(I) iodide (12.4 mg, 65 μmol) were added. The reaction mixture was heated at 120° C. for 22 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; gradient heptane-ethyl acetate) produced the title compound (10 mg, 27%). White semisolid, MS: 455.2 [M+H]+.
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