[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH2:19][CH2:18][C:17](=[O:20])[CH:16]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.CO>C1C=CC=CC=1.CCOCC>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH2:19][CH2:18][CH:17]([OH:20])[CH:16]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1To a solution 3-(3-Cyclopentyloxy-4-methoxyphenyl)cyclopent-2-en-1-one (275 mg, 1.01 mmol) (E7) in benzene (5 ml) at 0° C. under an argon atmosphere was added a toluene solution of diisobutylaluminum hydride (1M, 1.5 ml, 1.5 mmol) and the resulting mixture was stirred at 0° C. for 1 hr. The mixture was treated with methanol (5 ml) , poured into ether (100 ml) , filtered and concentrated under reduced pressure. The crude product was combined with the product to a similar reaction conducted on 55 mg of ketone and was purified by flash chromatography, eluting with 5:3.5:1 hexanes/ether/methylene chloride to provide a solid. Recrystallization from hexanes/ether provided the title compound (92 mg, 27.7%): m.p. 105°-107° C.; an additional 150 mg was recovered from the mother liquor.
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