Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([CH3:21])([CH3:20])[CH2:14][CH2:15][C:16]2=[O:19])=[CH:11][CH:10]=1>C1C=CC=CC=1.[Zn]>[OH:19][C:16]1([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([Br:8])[CH:18]=2)[C:13]([CH3:21])([CH3:20])[CH2:14][CH2:15]1To a suspension of Zn (1.20 g, 18.4 mmol) in 10 mL benzene at 100° C. was slowly added a solution of ethyl 2-bromoacetate (658.0 mg, 3.94 mmol) and 3,4-dihydro-4,4-dimethyl-7-bromo-naphthalen-1(2H)-one (Compound G, 500.0 mg, 1.97 mmol) in 20.0 mL benzene. The resulting mixture was heated for 2 h, cooled to room temperature, and the solution decanted from the residual solids. The solids were washed with EtOAc and the combined organic layers were washed with cold 15% H2SO4, saturated aqueous NaHCO3, and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents undr reduced pressure and column chromatography (10% EtOAc-hexanes) afforded the title compound as a yellow oil.
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