[BH4-].[Na+].[C:3]([O:11][C@@H:12]1[CH2:20][C@@H:15]2[O:16][C:17](=[O:19])[CH2:18][C@@H:14]2[C@H:13]1[CH:21]=[O:22])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:3]([O:11][C@@H:12]1[CH2:20][C@@H:15]2[O:16][C:17](=[O:19])[CH2:18][C@@H:14]2[C@@H:13]1[CH2:21][OH:22])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
To a suspension of sodium borohydride (650 mg, 17.1 mmol) in methanol (20 mL) at 0° C. (bath temperature) was added a solution of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one-4-carboxaldehyde (1) (3.5 g, 12.8 mmol) as a solution in 1:1 methanol:methylene chloride (40 mL). After 25 min, saturated citric acid was added cautiously (60 mL), the mixture was extracted with ethyl acetate (3×40 mL), the combined organic layers were washed with water (2×80 mL) and saturated brine (2×80 mL), dried (magnesium sulfate), filtered, and concentrated to afford 2 (2.43 g, 69%).
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