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 3,5-cyclosteroid have led to 3-acetoxy-16,23-epoxy-5H-21,24-dinorchol-5-en-6-one and 3-acetoxy-5-hydroxy-16,23-epoxy-21,24-dinorchol-5-en-6-one.N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 732–735, November–December, 1983.