In a preceding publication (1), the transformation of pregnane-20one-3(/3), 5,6(frans)-triol into pregnane-3,20-dione-5, 6(frons)-diol 6-monoacetate was discussed. This series of reactions involved the partial saponification of the 3,6-diacetate of the 3,5,6-triol and the subsequent oxidation with chromic acid of the 6-monoacetate. We have been interested in utilizing other methods which lead to the two possible partial oxidation-products of 3,5,6-triols, namely, the corresponding 3-one-5,6diols or 6-one-3,5-diols. A simple procedure would obviously consist in the partial oxidation by chromic acid of the free 3,5,6-triols. It remains to be shown whether such an oxidation always attacks the same carbon atom preferentially, regardless of the configurations at carbon atoms 3, 5, and 6, or whether the course of this reaction is determined by the stereochemical arrangement at the asymmetric centers mentioned.
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