Transformed steroids. 133. Synthesis of 20-deoxysteroids with a tetrahydropyran ring E
- 22 Downloads
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
Unable to display preview. Download preview PDF.
- 1.D. C. Rohrer, D. F. Fullerton, K. Yoshioka, A. H. From, and K. Ahmed, ACS Symp. Ser., No. 112, 259 (1979).Google Scholar
- 2.A. V. Kamernitskii, I. G. Reshetova, N. M. Mirsalikhova, and F. T. Umarova, Biokhimiya,47, No. 6, 957 (1982).Google Scholar
- 3.A. A. Akhrem, A. V. Kamernitskii, I. G. Reshetova, and K. Yu. Chernyuk, Izv. Akad. Nauk SSSR, Ser. Khim., 1633 (1973).Google Scholar
- 8.A. V. Kamernitskii, V. G. Levi, and I. G. Reshetova, Izv. Akad. Nauk SSSR, Ser. Khim., 887 (1981).Google Scholar