A-homopregnanes and 5β-methylpregnanes were prepared from the easily available 3β-hydroxy-20β-acetoxy-4β,5β-methylenepregnane by cationic and radical rearrangements respectively. The A-homopregnane was formed in a single step upon spontaneous rearrangement and elimination by treatment of the cyclopropyl alcohol with BF3·Et2O. The 5β-methylpregnane was obtained by cleavage of the hydrazone of the corresponding cyclopropylketone followed by rearrangement mediated by mercury(II) hydrides. ©ARKAT.
Documento: | Artículo |
Título: | Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes |
Autor: | Di Chenna, P.H.; Dansey, V.; Ghini, A.A.; Burton, G. |
Filiación: | Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas Y Naturales, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina |
Palabras clave: | 5β-methylpregnane; A-homopregnane; Cyclopropylcarbinyl cation; Cyclopropylcarbinyl radical |
Año: | 2005 |
Volumen: | 2005 |
Número: | 12 |
Página de inicio: | 154 |
Página de fin: | 162 |
Título revista: | Arkivoc |
Título revista abreviado: | Arkivoc |
ISSN: | 14246376 |
PDF: | https://bibliotecadigital.exactas.uba.ar/download/paper/paper_14246376_v2005_n12_p154_DiChenna.pdf |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p154_DiChenna |