Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona

Detalhes bibliográficos
Autor(a) principal: Iglesias Arteaga,Martín A.
Data de Publicação: 1997
Outros Autores: Leliebre Lara,Vivian, Pérez Martínez,Carlos, Coll Manchado,Francisco
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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spelling 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
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