Racemic synthesis of 1,2-secomicrominutinin

Detalhes bibliográficos
Autor(a) principal: Silva,Rosangela da
Data de Publicação: 2005
Outros Autores: Donate,Paulo Marcos, Silva,Gil Valdo José da, Pedersoli,Susimaire, Alemán,Carlos
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=S0103-50532005000400021
Resumo: The racemic 1,2-secomicrominutinin (25) was synthesized employing the intramolecular cycloaddition reaction of an (alkenyloxy)ketene, prepared from the corresponding tosylate. The (alkenyloxy)ketene undergoes intramolecular [2+2] cycloaddition to give tricyclic benzocyclobutafuranone (16), which by Baeyer-Villiger oxidation gives a benzofuranofuranone (17). Reaction of the latter compound with methyl propiolate, catalyzed by triphenylphosphine, produced the cinnamic ester derivative (25).
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spelling Racemic synthesis of 1,2-secomicrominutinin1,2-secomicrominutininbenzofuranofuranintramolecular cycloadditionsynthesisThe racemic 1,2-secomicrominutinin (25) was synthesized employing the intramolecular cycloaddition reaction of an (alkenyloxy)ketene, prepared from the corresponding tosylate. The (alkenyloxy)ketene undergoes intramolecular [2+2] cycloaddition to give tricyclic benzocyclobutafuranone (16), which by Baeyer-Villiger oxidation gives a benzofuranofuranone (17). Reaction of the latter compound with methyl propiolate, catalyzed by triphenylphosphine, produced the cinnamic ester derivative (25).Sociedade Brasileira de Química2005-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000400021Journal of the Brazilian Chemical Society v.16 n.3b 2005reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532005000400021info:eu-repo/semantics/openAccessSilva,Rosangela daDonate,Paulo MarcosSilva,Gil Valdo José daPedersoli,SusimaireAlemán,Carloseng2005-08-11T00:00:00Zoai:scielo:S0103-50532005000400021Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2005-08-11T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Racemic synthesis of 1,2-secomicrominutinin
title Racemic synthesis of 1,2-secomicrominutinin
spellingShingle Racemic synthesis of 1,2-secomicrominutinin
Silva,Rosangela da
1,2-secomicrominutinin
benzofuranofuran
intramolecular cycloaddition
synthesis
title_short Racemic synthesis of 1,2-secomicrominutinin
title_full Racemic synthesis of 1,2-secomicrominutinin
title_fullStr Racemic synthesis of 1,2-secomicrominutinin
title_full_unstemmed Racemic synthesis of 1,2-secomicrominutinin
title_sort Racemic synthesis of 1,2-secomicrominutinin
author Silva,Rosangela da
author_facet Silva,Rosangela da
Donate,Paulo Marcos
Silva,Gil Valdo José da
Pedersoli,Susimaire
Alemán,Carlos
author_role author
author2 Donate,Paulo Marcos
Silva,Gil Valdo José da
Pedersoli,Susimaire
Alemán,Carlos
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Silva,Rosangela da
Donate,Paulo Marcos
Silva,Gil Valdo José da
Pedersoli,Susimaire
Alemán,Carlos
dc.subject.por.fl_str_mv 1,2-secomicrominutinin
benzofuranofuran
intramolecular cycloaddition
synthesis
topic 1,2-secomicrominutinin
benzofuranofuran
intramolecular cycloaddition
synthesis
description The racemic 1,2-secomicrominutinin (25) was synthesized employing the intramolecular cycloaddition reaction of an (alkenyloxy)ketene, prepared from the corresponding tosylate. The (alkenyloxy)ketene undergoes intramolecular [2+2] cycloaddition to give tricyclic benzocyclobutafuranone (16), which by Baeyer-Villiger oxidation gives a benzofuranofuranone (17). Reaction of the latter compound with methyl propiolate, catalyzed by triphenylphosphine, produced the cinnamic ester derivative (25).
publishDate 2005
dc.date.none.fl_str_mv 2005-06-01
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=S0103-50532005000400021
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000400021
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532005000400021
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.16 n.3b 2005
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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