Dehydrierung von Steroiden, XII. Über die Behandlung von Cholesterin mit Floridin

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Abstract
According to Raoul and coworkers, the treatment of cholesterol with Floridln results in 9,10-seco-sterolds. We could not confirm these results with Florex XXS or Floridin XXF. In order to decide whether, in our reaction mixtures, 9,10-seco-steroids were produced at all, a method was developed, which permitted the detection of 9,10-seco-steroids admixed with large amounts of steroids with an intact ring system. The basis of the method is the different behavior of the chloranil dehydrogenatlon products of the steroids (17-H-cyclopenta[a]phenanthrene hydrocarbons from steroids with an intact ring system; styrylindene hydrocarbons from 9,10-seco-sterolds) upon oxidative cleavage with ozone. Only the dehydrogenatton products of 9,10-seco-sterolds can yield the mono-functional o-tolylic acid, which can be separated from di- and tri-carboxylic acids by ion exchange chromatography on Ecteola. After using this method on the reaction products from cholesterol with floridin (reaction carried out several times on 10 g. quantities of cholesterol), o-tolylic acid could not be unequivocally demonstrated. The reaction mixtures thus contained less than 0.25% (probably less than 0.1%) of 9,10-seco-steroid. The products from the reaction of 7-dehydrocholesterol and ergoserol with Floridin also yielded no o-tolyic acid.

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