[CH3:1][CH:2]([C:4]1[C:5](=[O:21])[CH2:6][C:7]([CH3:20])=[CH:8][CH2:9][CH2:10][C:11]([CH3:19])=[CH:12][CH2:13][CH2:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.O>C1(C)C=CC=CC=1>[CH3:19][C:11]1=[CH:12][CH2:13][CH2:14][C:15]([CH3:18])=[CH:16][CH:17]=[C:4]([CH:2]([CH3:1])[CH3:3])[C@@H:5]([OH:21])[CH2:6][C:7]([CH3:20])=[CH:8][CH2:9][CH2:10]1Under argon atmosphere, to a solution of the ketone, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-on (137 mg, 0.48 mmol) prepared in Reference Example 8 in dry toluene (25 ml) is dropwise added a 1 M solution of diisobutylaluminum hydride in toluene (0.6 ml) while stirring on a refrigerant bath at -70° C. After 1 hour, disappearance of the starting compound is confirmed. To the mixture is added water (0.25 ml) and the mixture is stirred enough after removing the bath. The mixture is dried over anhydrous magnesium sulfate, stirred, filtered and concentrated. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate =12:1) to give the desired Sarcophytol A (125 mg, 88%).
Loading…
