Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone

3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue...

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Autores principales: Eduardo, S.L., Ghini, A.A., Burton, G.
Formato: Artículo publishedVersion
Publicado: 2003
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Acceso en línea:http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p468_Eduardo
http://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2003_n10_p468_Eduardo_oai
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spelling I28-R145-paper_14246376_v2003_n10_p468_Eduardo_oai2020-10-19 Eduardo, S.L. Ghini, A.A. Burton, G. 2003 3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue was obtained as a byproduct upon cyclization of the isomeric 3α,4α-epoxide. 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_v2003_n10_p468_Eduardo info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar Arkivoc 2003;2003(10):468-476 2,19-Oxido-allopregnanolone 4,19-oxido-allopregnanolone Neurosteroid Oxido-bridged steroid 19 hydroxy 2alpha,3alpha epoxypregnane 19 hydroxypregnenolone 3 acetate 3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one 3alpha hydroxy 5alphah pregnan 20 one 4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one bridged compound neurosteroid silane derivative unclassified drug article cyclization desilylation drug structure drug synthesis structure activity relation Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion http://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2003_n10_p468_Eduardo_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 2,19-Oxido-allopregnanolone
4,19-oxido-allopregnanolone
Neurosteroid
Oxido-bridged steroid
19 hydroxy 2alpha,3alpha epoxypregnane
19 hydroxypregnenolone 3 acetate
3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one
3alpha hydroxy 5alphah pregnan 20 one
4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one
bridged compound
neurosteroid
silane derivative
unclassified drug
article
cyclization
desilylation
drug structure
drug synthesis
structure activity relation
spellingShingle 2,19-Oxido-allopregnanolone
4,19-oxido-allopregnanolone
Neurosteroid
Oxido-bridged steroid
19 hydroxy 2alpha,3alpha epoxypregnane
19 hydroxypregnenolone 3 acetate
3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one
3alpha hydroxy 5alphah pregnan 20 one
4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one
bridged compound
neurosteroid
silane derivative
unclassified drug
article
cyclization
desilylation
drug structure
drug synthesis
structure activity relation
Eduardo, S.L.
Ghini, A.A.
Burton, G.
Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
topic_facet 2,19-Oxido-allopregnanolone
4,19-oxido-allopregnanolone
Neurosteroid
Oxido-bridged steroid
19 hydroxy 2alpha,3alpha epoxypregnane
19 hydroxypregnenolone 3 acetate
3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one
3alpha hydroxy 5alphah pregnan 20 one
4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one
bridged compound
neurosteroid
silane derivative
unclassified drug
article
cyclization
desilylation
drug structure
drug synthesis
structure activity relation
description 3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue was obtained as a byproduct upon cyclization of the isomeric 3α,4α-epoxide.
format Artículo
Artículo
publishedVersion
author Eduardo, S.L.
Ghini, A.A.
Burton, G.
author_facet Eduardo, S.L.
Ghini, A.A.
Burton, G.
author_sort Eduardo, S.L.
title Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title_short Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title_full Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title_fullStr Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title_full_unstemmed Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title_sort oxido-bridged neurosteroid analogues. synthesis of 2,19-oxido-allopregnanolone
publishDate 2003
url http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p468_Eduardo
http://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14246376_v2003_n10_p468_Eduardo_oai
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