Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin

Detalhes bibliográficos
Autor(a) principal: Costa,Maísa B.
Data de Publicação: 2018
Outros Autores: Martins,Marcos P., Araújo,Hugo C. de, Resck,Inês S.
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=S0103-50532018000100074
Resumo: A convenient procedure for the synthesis and expansion of bicyclic rings has been developed for the production of probable precursors of non-racemic pyrenophorin, an antibiotic dilactone. The major highlight for this new synthetic methodology came from the use of a readily available reagent of easy manipulation, 9-oxabicyclo[3.3.1]nonane-2,6-diol, for the preparation of the bicyclic intermediate, which sequentially was subjected to oxidative cleavage with butyl nitrite resulted in an isomeric mixture, a dioximedilactone and diisoxazoledilactone.
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spelling Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorinenol etherring expansionmacrolidespyrenophorinA convenient procedure for the synthesis and expansion of bicyclic rings has been developed for the production of probable precursors of non-racemic pyrenophorin, an antibiotic dilactone. The major highlight for this new synthetic methodology came from the use of a readily available reagent of easy manipulation, 9-oxabicyclo[3.3.1]nonane-2,6-diol, for the preparation of the bicyclic intermediate, which sequentially was subjected to oxidative cleavage with butyl nitrite resulted in an isomeric mixture, a dioximedilactone and diisoxazoledilactone.Sociedade Brasileira de Química2018-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100074Journal of the Brazilian Chemical Society v.29 n.1 2018reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20170114info:eu-repo/semantics/openAccessCosta,Maísa B.Martins,Marcos P.Araújo,Hugo C. deResck,Inês S.eng2018-02-08T00:00:00Zoai:scielo:S0103-50532018000100074Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2018-02-08T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin
title Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin
spellingShingle Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin
Costa,Maísa B.
enol ether
ring expansion
macrolides
pyrenophorin
title_short Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin
title_full Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin
title_fullStr Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin
title_full_unstemmed Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin
title_sort Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin
author Costa,Maísa B.
author_facet Costa,Maísa B.
Martins,Marcos P.
Araújo,Hugo C. de
Resck,Inês S.
author_role author
author2 Martins,Marcos P.
Araújo,Hugo C. de
Resck,Inês S.
author2_role author
author
author
dc.contributor.author.fl_str_mv Costa,Maísa B.
Martins,Marcos P.
Araújo,Hugo C. de
Resck,Inês S.
dc.subject.por.fl_str_mv enol ether
ring expansion
macrolides
pyrenophorin
topic enol ether
ring expansion
macrolides
pyrenophorin
description A convenient procedure for the synthesis and expansion of bicyclic rings has been developed for the production of probable precursors of non-racemic pyrenophorin, an antibiotic dilactone. The major highlight for this new synthetic methodology came from the use of a readily available reagent of easy manipulation, 9-oxabicyclo[3.3.1]nonane-2,6-diol, for the preparation of the bicyclic intermediate, which sequentially was subjected to oxidative cleavage with butyl nitrite resulted in an isomeric mixture, a dioximedilactone and diisoxazoledilactone.
publishDate 2018
dc.date.none.fl_str_mv 2018-01-01
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=S0103-50532018000100074
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100074
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20170114
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.29 n.1 2018
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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