Alcaloides stéroïdiques—CLXVI : Synthese d'azides tertiaires en serie alicyclique-II. Mechanisme de formation et isomerisation des azido-5α et 5β pregnanes |
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| Authors: | Q Khuong-Huu A Pancrazi L Kabore |
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| Institution: | Institut de Chimie des Substances Naturelles du C.N.R.S., 91190, Gif sur Yvette, France |
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| Abstract: | Treatment of 6β-hydroxy 5α -prégnane by N3H/BF3-etherate/benzene gave 5α and 5β-azido prégnanes with C5→C6 hydride transfer. The kinetic product was 5α-azido pregnane which epimerized into a thermodynamic mixture 5α-azido rlarr2; 5β-azido. N3H Assistance was necessary for epimerization. Chemical degradation and 13C NMR study supported these structural assignments. |
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