Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrina

Detalhes bibliográficos
Autor(a) principal: Santos,Kelly de Oliveira
Data de Publicação: 2007
Outros Autores: Craveiro,Marcus Vinícius, Berlinck,Roberto G. S.
Tipo de documento: Artigo
Idioma: por
Título da fonte: Química Nova (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422007000800018
Resumo: We report the synthesis of amino(2-hydroxy-2-(4-methoxyphenyl)ethylamino)methaniminium (14) as a direct precursor of a tubastrine derivative (3-dehydroxy-4-methoxytubastrine). The synthetic steps involved functional group interconversions starting from 1-(4-methoxyphenyl)ethanone to obtain the guanidine-protected derivative 13. Tentative dehydration of 13 with SiOH-adsorbed CuSO4 resulted in guanidine deprotection only. This was an unexpected result, since there are no reports of CuSO4.SiOH as Boc-deprotecting of guanidines. The product 14 was obtained in five steps and 5.4 % overall yield, and constitutes a direct precursor of 3-dehydroxy-4-methoxytubastrine.
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spelling Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrinatubastrine3-dehydroxy-4-methoxy tubastrineguanidineWe report the synthesis of amino(2-hydroxy-2-(4-methoxyphenyl)ethylamino)methaniminium (14) as a direct precursor of a tubastrine derivative (3-dehydroxy-4-methoxytubastrine). The synthetic steps involved functional group interconversions starting from 1-(4-methoxyphenyl)ethanone to obtain the guanidine-protected derivative 13. Tentative dehydration of 13 with SiOH-adsorbed CuSO4 resulted in guanidine deprotection only. This was an unexpected result, since there are no reports of CuSO4.SiOH as Boc-deprotecting of guanidines. The product 14 was obtained in five steps and 5.4 % overall yield, and constitutes a direct precursor of 3-dehydroxy-4-methoxytubastrine.Sociedade Brasileira de Química2007-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422007000800018Química Nova v.30 n.8 2007reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0100-40422007000800018info:eu-repo/semantics/openAccessSantos,Kelly de OliveiraCraveiro,Marcus ViníciusBerlinck,Roberto G. S.por2008-01-21T00:00:00Zoai:scielo:S0100-40422007000800018Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2008-01-21T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrina
title Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrina
spellingShingle Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrina
Santos,Kelly de Oliveira
tubastrine
3-dehydroxy-4-methoxy tubastrine
guanidine
title_short Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrina
title_full Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrina
title_fullStr Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrina
title_full_unstemmed Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrina
title_sort Desenvolvimento de abordagem objetivando a síntese da 3-desidroxi-4-metoxi-tubastrina
author Santos,Kelly de Oliveira
author_facet Santos,Kelly de Oliveira
Craveiro,Marcus Vinícius
Berlinck,Roberto G. S.
author_role author
author2 Craveiro,Marcus Vinícius
Berlinck,Roberto G. S.
author2_role author
author
dc.contributor.author.fl_str_mv Santos,Kelly de Oliveira
Craveiro,Marcus Vinícius
Berlinck,Roberto G. S.
dc.subject.por.fl_str_mv tubastrine
3-dehydroxy-4-methoxy tubastrine
guanidine
topic tubastrine
3-dehydroxy-4-methoxy tubastrine
guanidine
description We report the synthesis of amino(2-hydroxy-2-(4-methoxyphenyl)ethylamino)methaniminium (14) as a direct precursor of a tubastrine derivative (3-dehydroxy-4-methoxytubastrine). The synthetic steps involved functional group interconversions starting from 1-(4-methoxyphenyl)ethanone to obtain the guanidine-protected derivative 13. Tentative dehydration of 13 with SiOH-adsorbed CuSO4 resulted in guanidine deprotection only. This was an unexpected result, since there are no reports of CuSO4.SiOH as Boc-deprotecting of guanidines. The product 14 was obtained in five steps and 5.4 % overall yield, and constitutes a direct precursor of 3-dehydroxy-4-methoxytubastrine.
publishDate 2007
dc.date.none.fl_str_mv 2007-01-01
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=S0100-40422007000800018
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422007000800018
dc.language.iso.fl_str_mv por
language por
dc.relation.none.fl_str_mv 10.1590/S0100-40422007000800018
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.30 n.8 2007
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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