C[C:2]1(C)[CH2:12][C:11](=O)[C:5]2[C:6]([CH2:9][OH:10])=[CH:7][O:8][C:4]=2[CH2:3]1.[Li]CCCC.CCOC(C)=O>C1COCC1>[O:8]1[C:4]2[CH:3]=[CH:2][CH:12]=[CH:11][C:5]=2[C@H:6]([CH2:9][OH:10])[CH2:7]1The crude oxirane 19 from above (2.4 g, 7.84 mmol) is dissolved in 50 ml of THF and cooled to −78° C. in a dry-ice bath. At this temperature, n-BuLi (1.6M in hexane, 4.9 ml, 7.84 mmol) is added drop wise. The mixture is then stirred for one hour and allowed to warm up to 0° C. After careful hydrolysis and extraction with EtOAc the crude is purified by Flash-chromatography (ethyl acetate/hexanes (from 5:95 to 25:75), silicagel).
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