Cortisone side chain degradation

Since we had shown that C. simplex dehydrogenated without concomitant side-chain degradation, we were able to use this transformation to prepare the previously unknown 1-dehydro analogs of cortisone and hydrocortisone, later named prednisone and prednisolone, respectively. These were tested in animals by Tolksdorf, Perlman,... 

Sodium bismuthate Oxidative degradation of cortisone side chains... 

Dry 3/ -acetoxy-ZI8,23-lanostadiene-24-ol-21-oic acid 21- 24-lactone added to a dry suspension of 10%-Pd-on-charcoal in p-cymene, and refluxed 2 hrs. with stirring under N2 3/ -acetoxy-zl8,20(22),23.lanostatrien-24-ol-21-oic acid 21 24-lactone. Y 75%.—This is part of a procedure to obtain the cortisone side chain by degradation. D. Rosenthal et al., Am. Soc. 85, 3971 (1963). 

An attractive route was based on hecogenin (55), freely available from the East African sisal plant, (ref.50) by conversion to the dibromide which was transformed to the 12-hydroxy-11-one and thence as the diacetate by reduction to the ll-keto compound shown in an overall yield of 55% from hecogenin. Side-chain Marker degradation afforded cortisone (ref.51) after further steps. 

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