[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C:7](=[O:12])[CH2:6][CH2:5]2.I[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:19](=O)([O-])[O-].[Cs+].[Cs+].O.CC[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[C:33]([O:36][CH2:37]C)(=[O:35])[CH3:34]>CN(C=O)C>[O:12]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:32][CH2:31][CH2:30][CH2:29][CH3:28])=[C:10]([O:11][CH2:18][C:17]3[CH:19]=[C:34]([CH:14]=[CH:15][CH:16]=3)[C:33]([O:36][CH3:37])=[O:35])[CH:9]=2)[CH2:5][CH2:6]1A mixture of 5,6-dihydroxyindanone (2.2 g; 13.4 mmol), iodopentane (1.75 ml; 13.4 mmol) and caesium carbonate (Cs2CO3; 4.8 g; 14.7 mmol) in DMF (50 ml) is heated at 40° C. for 35 minutes. The medium is cooled to room temperature, poured into water and extracted with methylene chloride. The combined organic phases are washed with water, dried over sodium sulfate and then concentrated (1.9 g solid). Flash chromatography (85/15 heptane/ethyl acetate) gives the expected product (1.5 g; 48% yield).
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