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

Autores
Di Chenna, P.H.; Dansey, V.; Ghini, A.A.; Burton, G.
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Fuente
Arkivoc 2005;2005(12):154-162
Materia
5β-methylpregnane
A-homopregnane
Cyclopropylcarbinyl cation
Cyclopropylcarbinyl radical
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/2.5/ar
Repositorio
Biblioteca Digital (UBA-FCEN)
Institución
Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
OAI Identificador
paperaa:paper_14246376_v2005_n12_p154_DiChenna
Acceder
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network_acronym_str BDUBAFCEN
repository_id_str 1896
network_name_str Biblioteca Digital (UBA-FCEN)
spelling Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanesDi Chenna, P.H.Dansey, V.Ghini, A.A.Burton, G.5β-methylpregnaneA-homopregnaneCyclopropylcarbinyl cationCyclopropylcarbinyl radicalA-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.2005info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttp://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p154_DiChennaArkivoc 2005;2005(12):154-162reponame:Biblioteca Digital (UBA-FCEN)instname:Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturalesinstacron:UBA-FCENenginfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/2.5/ar2025-09-11T10:21:21Zpaperaa:paper_14246376_v2005_n12_p154_DiChennaInstitucionalhttps://digital.bl.fcen.uba.ar/Universidad públicaNo correspondehttps://digital.bl.fcen.uba.ar/cgi-bin/oaiserver.cgiana@bl.fcen.uba.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:18962025-09-11 10:21:22.639Biblioteca Digital (UBA-FCEN) - Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturalesfalse
dc.title.none.fl_str_mv Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes
title Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes
spellingShingle Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes
Di Chenna, P.H.
5β-methylpregnane
A-homopregnane
Cyclopropylcarbinyl cation
Cyclopropylcarbinyl radical
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
dc.creator.none.fl_str_mv Di Chenna, P.H.
Dansey, V.
Ghini, A.A.
Burton, G.
author Di Chenna, P.H.
author_facet Di Chenna, P.H.
Dansey, V.
Ghini, A.A.
Burton, G.
author_role author
author2 Dansey, V.
Ghini, A.A.
Burton, G.
author2_role author
author
author
dc.subject.none.fl_str_mv 5β-methylpregnane
A-homopregnane
Cyclopropylcarbinyl cation
Cyclopropylcarbinyl radical
topic 5β-methylpregnane
A-homopregnane
Cyclopropylcarbinyl cation
Cyclopropylcarbinyl radical
dc.description.none.fl_txt_mv 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.
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.
publishDate 2005
dc.date.none.fl_str_mv 2005
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p154_DiChenna
url http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p154_DiChenna
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/2.5/ar
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/2.5/ar
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv Arkivoc 2005;2005(12):154-162
reponame:Biblioteca Digital (UBA-FCEN)
instname:Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
instacron:UBA-FCEN
reponame_str Biblioteca Digital (UBA-FCEN)
collection Biblioteca Digital (UBA-FCEN)
instname_str Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
instacron_str UBA-FCEN
institution UBA-FCEN
repository.name.fl_str_mv Biblioteca Digital (UBA-FCEN) - Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
repository.mail.fl_str_mv ana@bl.fcen.uba.ar
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score 13.004268

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