[Br:1]/[CH:2]=[C:3]1\[CH2:4][CH2:5][CH2:6][C@@:7]2([CH3:16])[C@H:11]\1[CH2:10][CH2:9][C@@H:8]2[C@H:12](C)[CH:13]=O.N1C=CC=CC=1C1C=CC=CN=1.C1N2CCN(CC2)C1.[O:37]=O.Cl>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1]/[CH:2]=[C:3]1\[CH2:4][CH2:5][CH2:6][C@@:7]2([CH3:16])[C@H:11]\1[CH2:10][CH2:9][C@@H:8]2[C:12](=[O:37])[CH3:13](S)-2-{(E,3R,3aR,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}propanal (Compound 10: 43 mg, 0.151 mmol) synthesized according to the method described in Org. Lett. 2003, 5, 4859-4862 was dissolved in dimethylformamide (300 μl), and copper (II) acetate (3.1 mg, 0.0171 mmol), bipyridyl (2.8 mg, 0.0179 mmol) and triethylenediamine (17.4 mg, 0.155 mmol) were added thereto. The resulting mixture was heated to 80° C. and stirred for 4 hours with streaming oxygen. After cooling the mixture to room temperature, 2N hydrochloric acid was added thereto, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and evaporated. The obtained product was purified by flash column chromatography to obtain 1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanone (24.1 mg, 58.8%).
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