Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes

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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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Autores principales:	Di Chenna, P.H., Dansey, V., Ghini, A.A., Burton, G.
Formato:	Artículo publishedVersion
Publicado:	2005
Materias:	5β-methylpregnane A-homopregnane Cyclopropylcarbinyl cation Cyclopropylcarbinyl radical
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p154_DiChenna https://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p154_DiChenna_oai
Aporte de:	Repositorio Digital de la Universidad de Buenos Aires (UBA) de Universidad de Buenos Aires

id	I28-R145-paper_14246376_v2005_n12_p154_DiChenna_oai
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spelling	I28-R145-paper_14246376_v2005_n12_p154_DiChenna_oai2024-08-16 Di Chenna, P.H. Dansey, V. Ghini, A.A. Burton, G. 2005 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. application/pdf http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p154_DiChenna info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar Arkivoc 2005;2005(12):154-162 5β-methylpregnane A-homopregnane Cyclopropylcarbinyl cation Cyclopropylcarbinyl radical Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion https://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p154_DiChenna_oai
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-145
collection	Repositorio Digital de la Universidad de Buenos Aires (UBA)
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 https://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2005_n12_p154_DiChenna_oai
work_keys_str_mv	AT dichennaph rearrangementof4b5bmethylenepregnanesasimpleapproachtoahomopregnanesand5bmethylpregnanes AT danseyv rearrangementof4b5bmethylenepregnanesasimpleapproachtoahomopregnanesand5bmethylpregnanes AT ghiniaa rearrangementof4b5bmethylenepregnanesasimpleapproachtoahomopregnanesand5bmethylpregnanes AT burtong rearrangementof4b5bmethylenepregnanesasimpleapproachtoahomopregnanesand5bmethylpregnanes
_version_	1809357022464835584

Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes

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