[Li+].[AlH4-].C([O:6][C@H:7]1[CH2:11][CH2:10][C@@H:9]([CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[CH2:13]2)[C@:8]1([CH3:28])[CH2:24][C:25](O)=[O:26])(=O)C.[OH-].[Na+].ClCCl>CCOCC.C1COCC1>[CH3:23][O:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([C@H:9]1[C@:8]([CH3:28])([CH2:24][CH2:25][OH:26])[C@@H:7]([OH:6])[CH2:11][CH2:10]1)[CH2:21][CH2:20]2
To a slurry of 0.420 g of lithium tetrahydro-aluminate(1-) in 400 ml of ether is slowly added, with stirring, a solution of 0.780 g of (1S,2S,5S)-2-acetoxy-5-(1,2,3,4-tetrahydro-6-methoxy-2-naphthyl)-1-methylcyclopentaneacetic acid in a mixture of 10 ml of diethyl ether and 5 ml of THF. When the addition is complete, stirring is continued at room temperature for 18 hours, whereupon 1.7 ml of aqueous 5% sodium hydroxide followed by 40 ml of dichloromethane is introduced. The resultant mixture is filtered. Solvent is stripped from the filtrate by vacuum distillation, leaving a white solid residue which, crystallized from a mixture of benzene and hexane, affords (1S,2S,5S)-5-(1,2,3,4-tetrahydro-6-methoxy-2-naphthyl)-2-hydroxy-1-methylcyclopentaneethanol melting at 151°-153° further characterized by a specific rotation of +62°.
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