Transformed steroids. 133. Synthesis of 20-deoxysteroids with a tetrahydropyran ring E
The synthesis of 20-deoxy compounds — the precursors of the steroid pyranols and pyranones synthesized by the authors previously — has been effected from a steroid 20-ketotetrahydropyran by the hydrogenolysis of the corresponding ethylene dithioketal with Raney nickel. The1H and13C NMR spectra have been studied in detail. Transformations of rings A and B via the epoxide or the 3,5α-cyclosteroid have led to 3-acetoxy-16β,23-epoxy-5αH-21,24-dinorchol-5-en-6-one and 3-acetoxy-5α-hydroxy-16β,23-epoxy-21,24-dinorchol-5-en-6-one.
KeywordsEtOAc Oleanolic Acid Sodium Periodate Raney Nickel Hederagenin
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