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Aside from biochemical means (2), C-ll oxygenated corticosteroids have so far only been prepared by partial synthesis from steroids already possessing an oxygen substituent in ring C (positions 11 or 12) (3). In view of the tremendous interest in the biological properties of cortisone and related C-ll oxygenated pregnane derivatives, it seemed important to accomplish the chemical introduction of an oxygen function at C-ll in steroids which possess no substituents in ring C and which comprise the vast majority of readily available, naturallyoccurring starting materials. The most obvious approach to this problem appeared to be the initial introduction of double bonds into or adjacent to ring C.Since the steroidal sapogenin side chain can be converted in two steps to the A16-20-keto moiety so useful for the elaboration of the dihydroxyacetone grouping characteristic of cortisone and related substances, it was especially desirable to study this approach in the sapogenin series and the present report deals with

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