[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[O:5][C:4](=[O:13])[C:3]=1[C:14](=[O:17])[CH2:15][CH3:16].[Na].C([O-])(O)=O.[Na+]>C(Cl)Cl.N1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH:11]=[O:12])[O:5][C:4](=[O:13])[C:3]=1[C:14](=[O:17])[CH2:15][CH3:16]To 4-hydroxy-6-(4-hydroxybutyl)-3-propionyl-2H-pyran-2-one (XV; 1.47 g; 6.12 mmol) in 60 ml CH2Cl2 and 2.19 ml pyridine, was added sodium periodinate (6.13 g; 15.3 mmol; Aldrich). The reaction was stirred at 28° C. for 3 h, neutralized with saturated NaHCO3, extracted with 3×150 ml CH2Cl2, dried with brine and Na2SO4, and evaporated. The product was purified via silica flash chromatography (20% EtOAc in hexanes).
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