CCCCCC.[H-].[K+].[OH:9][C:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[C:14]=2[CH:13]=[CH:12][CH:11]=1.S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:28][C@H:29]1[O:31][CH2:30]1)(=O)=O>C1COCC1>[O:31]1[CH2:30][C@H:29]1[CH2:28][O:9][C:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[C:14]=2[CH:13]=[CH:12][CH:11]=1A stirred suspension of hexane washed potassium hydride (0.204 g, 5 mmol) in THF was treated in one portion with 4-hydroxy-9-fluorenone (1.0 g, 5.1 mmol). To the purple suspension was added (S)-glycidyl nosylate (1.0 g, 5 mmol) and the mixture was stirred at ambient temperature overnight. The reaction was partitioned with EtOAc. The organic phase was washed with H2O, brine and dried (Na2SO4). The solvent was removed in vacuo to provide crude product. Purification by flash chromatography (CH2Cl2-hexane 3:1) provided 0.210 g of product as a yellow solid.
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