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Inicio » Actividades I+D > Publicaciones 2003 > PhI=NSes Mediated Aziridination of 11-Pr...
artículo con referato
"PhI=NSes Mediated Aziridination of 11-Pregnane Derivatives: Synthesis of an 11,12-Aziridino Analogue of Neuroactive Steroids"
P.H. Di Chenna, P. Dauban, A. Ghini, R. Baggio, M.T. Garland, G. Burton and R.H. Dodd
Tetrahedron 59(7) (2003) 1009-1014
Reaction of 11-pregnene-3,20-dione (6)or 3-a-acetoxy-11-pregnen-20-one (12) with trimethylsilyle-thanesulfonyl (“Ses”) iminoiodinane 5 in the presence of copper (I) triflate gave the corresponding a,a-11,12-aziridino steroids 7 and 13 in 53 and 45% yields, respectively. The Ses group of each compound was removed using the TASF reagent and the resulting free aziridine NH was methylated to afford the 11a,12a-N-methyl aziridinosteroids 9 and 15, respectively. The latter is a conformationally constrained analogue of the endogenous neurosteroid pregnanolone (1).
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