Experimental

3-((tert-butyldimethylsilyl)oxy)-2-chloro-7,7-dimethyl-7a-(4-(trimethylsilyl)- but-3-yn-1-yl)-7,7a-dihydro-1H-inden-5(6H)-one 3 (30.4 mg, 51%) 3: silyl enol ether 18 was combined with Mioskowski’s reagent (Bu4NCl3) (1.0 mL, 2.4 eqiv.) and CH2Cl2 (1.05 mL, 2.4 equiv) at -78O C. The mixture was allowed to come to room temperature over the course of 5 hours. Then, the mixture was hydrated with saturated, aqueous NaHCO3 (10 mL). The aqueous phase was extracted with diethyl ether (3 x 40 mL). The organic extracts were combined with saturated, aqueous NaCl (1 x 10 mL) and dried with MgSO4. The product was filtered and concentrated under negative pressure. Column chromatography (EtOAc/hexanes 1:9) was used to purify the product. 3-((tert-butyldimethylsilyl)oxy)-2-chloro-7,7-dimethyl-7a-(4-(trimethylsilyl)- but-3-yn-1-yl)-7,7a-dihydro-1H-inden-5(6H)-one 3 (30.4 mg, 51%). IR (thin film): 2960, 2933, 2900, 2860, 2176, 1658, 1628, 1603, 1472, 1464, 1442, 1390, 1372, 1338, 1316, 1277, 1250, 1216, 1158, 1127, 1092, 1039, 1004, 986, 919, 841, 786, 760, 698, 638 cm-1

 

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