[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([C:11]1([CH2:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)[CH3:10].O>CS(C)=O.C1COCC1>[CH2:9]([C:11]1([CH2:21][C:22]2([C:23]([F:24])([F:26])[F:25])[CH2:4][O:27]2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)[CH3:10]To a suspension of sodium hydride (74 mg of a 60% dispersion in mineral oil, 1.85 mmol) in DMSO (5 ml) was added a solution of trimethylsulphoxonium iodide (610 mg, 2.77 mmol) in DMSO (5 ml). After stirring at room temperature for 30 min a solution of 3-(1-ethyl-1,2,3,4-tetrahydro-1-naphthalenyl)-1,1,1-trifluoro-2-propanone (Intermediate 13) (500 mg, 1.85 mmol) in THF (3 ml) was added and the mixture was stirred at room temperature for 2 h. The reaction mixture was poured into water and extracted with diethylether. The organic extract was washed repeatedly with water, dried over anhydrous sodium sulphate and evaporated in vacuo to give the title compound as a crude mixture of diastereomers. Extraction of aqueous layer with dichloromethane yielded further title compound as a crude mixture of diastereomers. Combined products were then applied to a 20 g silica SPE cartridge eluting with a 0-10% dichloromethane in cyclohexane gradient for 10 min followed by 10% dichloromethane in cyclohexane for 5 min. This gave, in order of elution, Intermediate 14 (racemic diastereomer 1, 178 mg): and Intermediate 15 (racemic diastereomer 2, 86 mg).
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