The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative

Detalhes bibliográficos
Autor(a) principal: Silva,Alcides J. M. da
Data de Publicação: 2004
Outros Autores: Netto,Chaquip D., Costa,Paulo R. R.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000600029
Resumo: We report the first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, a natural isoflavonoid that shows antitumoral activity. The key step involved the Heck reaction between the 7,8-dibenzyloxychromen and the organomercurial derived from sesamol, followed by debenzylation. The Heck adduct was also employed in the synthesis of the corresponding coumestan derivative, using DDQ as oxidant agent.
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spelling The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivativeisoflavonoidspterocarpanDDQantitumoral agentscoumestanWe report the first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, a natural isoflavonoid that shows antitumoral activity. The key step involved the Heck reaction between the 7,8-dibenzyloxychromen and the organomercurial derived from sesamol, followed by debenzylation. The Heck adduct was also employed in the synthesis of the corresponding coumestan derivative, using DDQ as oxidant agent.Sociedade Brasileira de Química2004-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000600029Journal of the Brazilian Chemical Society v.15 n.6 2004reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532004000600029info:eu-repo/semantics/openAccessSilva,Alcides J. M. daNetto,Chaquip D.Costa,Paulo R. R.eng2005-01-24T00:00:00Zoai:scielo:S0103-50532004000600029Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2005-01-24T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative
title The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative
spellingShingle The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative
Silva,Alcides J. M. da
isoflavonoids
pterocarpan
DDQ
antitumoral agents
coumestan
title_short The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative
title_full The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative
title_fullStr The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative
title_full_unstemmed The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative
title_sort The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative
author Silva,Alcides J. M. da
author_facet Silva,Alcides J. M. da
Netto,Chaquip D.
Costa,Paulo R. R.
author_role author
author2 Netto,Chaquip D.
Costa,Paulo R. R.
author2_role author
author
dc.contributor.author.fl_str_mv Silva,Alcides J. M. da
Netto,Chaquip D.
Costa,Paulo R. R.
dc.subject.por.fl_str_mv isoflavonoids
pterocarpan
DDQ
antitumoral agents
coumestan
topic isoflavonoids
pterocarpan
DDQ
antitumoral agents
coumestan
description We report the first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, a natural isoflavonoid that shows antitumoral activity. The key step involved the Heck reaction between the 7,8-dibenzyloxychromen and the organomercurial derived from sesamol, followed by debenzylation. The Heck adduct was also employed in the synthesis of the corresponding coumestan derivative, using DDQ as oxidant agent.
publishDate 2004
dc.date.none.fl_str_mv 2004-12-01
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=S0103-50532004000600029
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000600029
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532004000600029
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 Journal of the Brazilian Chemical Society v.15 n.6 2004
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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