[C:1]([C:4]1[O:8][C:7]2[C:9](=[O:19])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[C:14]([OH:18])[CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2].C(Cl)Cl.C(N(CC)CC)C.C(O)=O>O.Cl>[OH:3][CH:1]([C:4]1[O:8][C:7]2[C:9](=[O:19])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[C:14]([OH:18])[CH:13]=[CH:12][CH:11]=3)[CH3:2]Into a flask were added 2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione (128 mg, 0.5 mmol), Ru[(S,S)-Tsdpen](p-cymene) (15 mg, 0.025 mmol, 5 mol %), methylene chloride (5 mL) and formic acid-triethylamine mixture (5:2, 1.3 ml). The resulting suspension mixture was stirred at room temperature for 24 hours, and then diluted with water and 10% aqueous hydrochloric acid solution. The aqueous layer was extracted with chloroform twice, and the extract was washed with water and a saturated aqueous sodium chloride solution sequentially, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to give 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione (NQ801) (115 mg, 89%, 96% ee) as a yellow crystal.
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