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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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 |
work_keys_str_mv |
AT eduardosl oxidobridgedneurosteroidanaloguessynthesisof219oxidoallopregnanolone AT ghiniaa oxidobridgedneurosteroidanaloguessynthesisof219oxidoallopregnanolone AT burtong oxidobridgedneurosteroidanaloguessynthesisof219oxidoallopregnanolone |
_version_ |
1766026767690104832 |