Abstract
The reduction of ketone9 with LiAl (t-BuO)3H in absolute THF gave alcohols11 and13, while the reduction of ketone9 with NaBH4 in THF-H2O gave an alcohol10. Alcohol11 on weak alkaline treatment was epimerized to10. Similarly, alcohol13 was epimerized to15 under similar conditions. Ketolactone ester20 was reduced with LiAl (t-BuO)3H in anhydrous solvent to give alcohol24, while it was reduced with NaBH4 in MeOH-H2O to give alcohol3. Alcohol24 was epimerized to3 in weak alkaline conditions. Two other epimeric alcohols29 and31 were derived from3via a series of reactions. Alcohol29 was epimerized to31 by treatment with weak alkali, although the reaction rate was much slower.
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