Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes
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 cyclopr...
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| Formato: | Artículo publishedVersion |
| Lenguaje: | Inglés |
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2005
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p154_DiChenna |
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paperaa:paper_14246376_v2005_n12_p154_DiChenna2023-06-12T16:50:09Z Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes Arkivoc 2005;2005(12):154-162 Di Chenna, P.H. Dansey, V. Ghini, A.A. Burton, G. 5β-methylpregnane A-homopregnane Cyclopropylcarbinyl cation Cyclopropylcarbinyl radical 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. Fil:Di Chenna, P.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Dansey, V. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ghini, A.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2005 info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion application/pdf eng info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p154_DiChenna |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| language |
Inglés |
| orig_language_str_mv |
eng |
| topic |
5β-methylpregnane A-homopregnane Cyclopropylcarbinyl cation Cyclopropylcarbinyl radical |
| spellingShingle |
5β-methylpregnane A-homopregnane Cyclopropylcarbinyl cation Cyclopropylcarbinyl radical Di Chenna, P.H. Dansey, V. Ghini, A.A. Burton, G. Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes |
| topic_facet |
5β-methylpregnane A-homopregnane Cyclopropylcarbinyl cation Cyclopropylcarbinyl radical |
| description |
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. |
| format |
Artículo Artículo publishedVersion |
| author |
Di Chenna, P.H. Dansey, V. Ghini, A.A. Burton, G. |
| author_facet |
Di Chenna, P.H. Dansey, V. Ghini, A.A. Burton, G. |
| author_sort |
Di Chenna, P.H. |
| title |
Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes |
| title_short |
Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes |
| title_full |
Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes |
| title_fullStr |
Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes |
| title_full_unstemmed |
Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes |
| title_sort |
rearrangement of 4β,5β-methylenepregnanes: a simple approach to a-homopregnanes and 5β-methylpregnanes |
| publishDate |
2005 |
| url |
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p154_DiChenna |
| work_keys_str_mv |
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1769810136568692736 |