[C:1]1([C:7]2[N:8]=[CH:9][S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].C(C1C=CC=CC=1)C.[O:28]1[C:32]2([CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]2)[O:31][CH2:30][CH2:29]1.C(=O)([O-])O.[Na+]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([C:35]3([OH:38])[CH2:36][CH2:37][C:32]4([O:31][CH2:30][CH2:29][O:28]4)[CH2:33][CH2:34]3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
4.5 g of 4-phenylthiazole were dissolved in 80 ml of anhydrous THF and 18.1 ml of a 2 M solution of lithium diisopropylamide in THF/HEP/ethylbenzene (Aldrich) were added dropwise at −70° C. The mixture was stirred at −70° C. for 60 min, then a solution of 4.4 g of 1,4-dioxaspiro[4.5]decan-8-one in 50 ml of anhydrous THF was added dropwise at −65° C. to −70° C. Subsequently, the mixture was warmed to room temperature, poured onto 120 ml of a saturated aqueous sodium hydrogencarbonate solution and extracted three times with 80 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 7.1 g of the title compound were obtained as a pale yellow oil.
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