Racemic synthesis of 1,2-secomicrominutinin
Autor(a) principal: | |
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Data de Publicação: | 2005 |
Outros Autores: | , , , |
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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Journal of the Brazilian Chemical Society (Online) |
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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 |
_version_ |
1750318166230171648 |