Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona
Autor(a) principal: | |
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Data de Publicação: | 1997 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | spa |
Título da fonte: | Química Nova (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40421997000400004 |
Resumo: | The synthesis of two new spirostanic analogs of the natural occurring brassinosteroid 6-desoxocastasterone (1) is described. The scheme consists in the formation and elimination of tigogenin mesylate followed by catalytic dihydroxylation of the resulting D2-steroid (3) and acetylation of the 2a, 3a-diol introduced.Treatment diacetate (5) with NaNO2/BF3.Et2O and chromatography in alumina led to a 23-keto (6) which on reduction produced the 23S alcohol (8) as major product. Saponification of the 2a, 3a-diacetoxy-23-keto compound (6) and the 2a,3a-diacetoxy-23-hydroxy compound (8) led to the spirobrasinosteroids (7) and (9).13C NMR and ¹H RMN characteristics derived from substitution at C23 are briefly discussed. |
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Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasteronaSpirobrassinosteroidssynthesisRMNThe synthesis of two new spirostanic analogs of the natural occurring brassinosteroid 6-desoxocastasterone (1) is described. The scheme consists in the formation and elimination of tigogenin mesylate followed by catalytic dihydroxylation of the resulting D2-steroid (3) and acetylation of the 2a, 3a-diol introduced.Treatment diacetate (5) with NaNO2/BF3.Et2O and chromatography in alumina led to a 23-keto (6) which on reduction produced the 23S alcohol (8) as major product. Saponification of the 2a, 3a-diacetoxy-23-keto compound (6) and the 2a,3a-diacetoxy-23-hydroxy compound (8) led to the spirobrasinosteroids (7) and (9).13C NMR and ¹H RMN characteristics derived from substitution at C23 are briefly discussed.Sociedade Brasileira de Química1997-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40421997000400004Química Nova v.20 n.4 1997reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0100-40421997000400004info:eu-repo/semantics/openAccessIglesias Arteaga,Martín A.Leliebre Lara,VivianPérez Martínez,CarlosColl Manchado,Franciscospa2008-09-08T00:00:00Zoai:scielo:S0100-40421997000400004Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2008-09-08T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona |
title |
Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona |
spellingShingle |
Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona Iglesias Arteaga,Martín A. Spirobrassinosteroids synthesis RMN |
title_short |
Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona |
title_full |
Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona |
title_fullStr |
Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona |
title_full_unstemmed |
Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona |
title_sort |
Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona |
author |
Iglesias Arteaga,Martín A. |
author_facet |
Iglesias Arteaga,Martín A. Leliebre Lara,Vivian Pérez Martínez,Carlos Coll Manchado,Francisco |
author_role |
author |
author2 |
Leliebre Lara,Vivian Pérez Martínez,Carlos Coll Manchado,Francisco |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Iglesias Arteaga,Martín A. Leliebre Lara,Vivian Pérez Martínez,Carlos Coll Manchado,Francisco |
dc.subject.por.fl_str_mv |
Spirobrassinosteroids synthesis RMN |
topic |
Spirobrassinosteroids synthesis RMN |
description |
The synthesis of two new spirostanic analogs of the natural occurring brassinosteroid 6-desoxocastasterone (1) is described. The scheme consists in the formation and elimination of tigogenin mesylate followed by catalytic dihydroxylation of the resulting D2-steroid (3) and acetylation of the 2a, 3a-diol introduced.Treatment diacetate (5) with NaNO2/BF3.Et2O and chromatography in alumina led to a 23-keto (6) which on reduction produced the 23S alcohol (8) as major product. Saponification of the 2a, 3a-diacetoxy-23-keto compound (6) and the 2a,3a-diacetoxy-23-hydroxy compound (8) led to the spirobrasinosteroids (7) and (9).13C NMR and ¹H RMN characteristics derived from substitution at C23 are briefly discussed. |
publishDate |
1997 |
dc.date.none.fl_str_mv |
1997-08-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40421997000400004 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40421997000400004 |
dc.language.iso.fl_str_mv |
spa |
language |
spa |
dc.relation.none.fl_str_mv |
10.1590/S0100-40421997000400004 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Química Nova v.20 n.4 1997 reponame:Química Nova (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Química Nova (Online) |
collection |
Química Nova (Online) |
repository.name.fl_str_mv |
Química Nova (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
quimicanova@sbq.org.br |
_version_ |
1750318100109066240 |