[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22](OC)=[O:23])[CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CCOCC.O>[CH2:7]([O:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[CH2:22][OH:23])[CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]35 mg of lithium aluminum hydride (922 μmol) are added, at 0° C., to 140 mg of 15 (460 μmol) in ether (3 mL). After reaction for 1 hour 30 minutes, the reaction medium is diluted with ether and hydrolyzed with two drops of water. After filtering through Celite, drying over Na2SO4 and concentrating, 127 mg of a colorless oil are isolated, i.e. a yield of 99%.
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