Transformed steroids. 123. Synthesis of 5α(H)- and 5α(OH)-6-ketosteroids with an additional 17α,20ξ-dihydroxytetrahydropyran ring E
- 33 Downloads
The paper is devoted to the synthesis of 3,17α,20-trihydroxy-16β,23-epoxy-21,24-dinor-5αH-cholan-6-one and 3,5α,17α,20-tetrahydroxy-16β,23-epoxy-21,24-dinorcholan-6-one and derivatives of them. It has been shown that the reduction of 3,17α-dihydroxy-16β,23-epoxy-21,24-dinorchol-5-en-20-one with sodium tetrahydroborate and with diborane takes place stereospecifically with different spatial directivities: in the products of diborane reduction, ring E exists in the boat form, as has been shown by1H and13C NMR methods. The trans linkage of rings A/B in the modified steroids has been confirmed by their circular dichroism spectra.
KeywordsEtOAc DMFA B2H6 Matrine Diborane
Unable to display preview. Download preview PDF.
- 1.A. V. Kamernitskii, N. M. Ol'gina, I. G. Reshetova, and K. Yu. Chernyuk, Izv. Akad. Nauk SSSR, Ser. Khim., 411 (1975).Google Scholar
- 2.A. V. Kamernitskii, V. A. Krivoruchko, and I. G. Reshitova, Khim. Prir. Soedin., 208 (1980).Google Scholar
- 5.N. S. Bhacca and D. H. Williams, Applications of NMR Spectroscopy in Organic Chemistry, Holden-Day, San Francisco (1964).Google Scholar
- 6.Yu. T. Struchkov, O. V. Lindeman, V. E. Shklover, M. Yu. Antipin, A. P. Polishchuk, V. A. Karapetyan, A. M. Turuta, I. G. Reshetov, and A. V. Kamernitskii, The Structural Investigation of Synthetic Steroid Hormones and Their Derivatives. Abstracts of Lectures at the IIIrd All-Union Conference on Organic Crystal Chemistry [in Russian], Gor'kii (1981).Google Scholar
- 13.A. V. Kamernitskii, V. A. Pavlov, I. G. Reshetova, and G. Snattske, Izv. Akad. Nauk SSSR, Ser. Khim.,1980, 2391 (1980).Google Scholar