Synthesis and expansion of bicyclic enol ether: a probable precursor for the synthesis of macrolide (±)-pyrenophorin

Detalhes bibliográficos
Autor(a) principal: Costa, Maísa Borges
Data de Publicação: 2018
Outros Autores: Martins, Marcos P., Araújo, Hugo Clemente de, Resck, Inês Sabioni
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UnB
Texto Completo: http://repositorio.unb.br/handle/10482/33450
http://dx.doi.org/10.21577/0103-5053.20170114
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 (±)-pyrenophorinQuímica orgânicaAntibióticosA 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 Química2019-01-02T13:52:01Z2019-01-02T13:52:01Z2018info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfCOSTA, Maísa B. et al. Synthesis and expansion of bicyclic enol ether: a probable precursor for the synthesis of macrolide (±)-pyrenophorin. Journal of the Brazilian Chemical Society, São Paulo, v. 29, n. 1, p. 74-78, jan. 2018. DOI: http://dx.doi.org/10.21577/0103-5053.20170114. Disponível em: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100074&lng=en&nrm=iso. Acesso em: 16 maio 2019.http://repositorio.unb.br/handle/10482/33450http://dx.doi.org/10.21577/0103-5053.20170114(CC BY) - This is an open-access article distributed under the terms of the Creative Commons Attribution License.info:eu-repo/semantics/openAccessCosta, Maísa BorgesMartins, Marcos P.Araújo, Hugo Clemente deResck, Inês Sabioniengreponame:Repositório Institucional da UnBinstname:Universidade de Brasília (UnB)instacron:UNB2023-06-04T22:18:55Zoai:repositorio.unb.br:10482/33450Repositório InstitucionalPUBhttps://repositorio.unb.br/oai/requestrepositorio@unb.bropendoar:2023-06-04T22:18:55Repositório Institucional da UnB - Universidade de Brasília (UnB)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 Borges
Química orgânica
Antibióticos
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 Borges
author_facet Costa, Maísa Borges
Martins, Marcos P.
Araújo, Hugo Clemente de
Resck, Inês Sabioni
author_role author
author2 Martins, Marcos P.
Araújo, Hugo Clemente de
Resck, Inês Sabioni
author2_role author
author
author
dc.contributor.author.fl_str_mv Costa, Maísa Borges
Martins, Marcos P.
Araújo, Hugo Clemente de
Resck, Inês Sabioni
dc.subject.por.fl_str_mv Química orgânica
Antibióticos
topic Química orgânica
Antibióticos
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
2019-01-02T13:52:01Z
2019-01-02T13:52:01Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv COSTA, Maísa B. et al. Synthesis and expansion of bicyclic enol ether: a probable precursor for the synthesis of macrolide (±)-pyrenophorin. Journal of the Brazilian Chemical Society, São Paulo, v. 29, n. 1, p. 74-78, jan. 2018. DOI: http://dx.doi.org/10.21577/0103-5053.20170114. Disponível em: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100074&lng=en&nrm=iso. Acesso em: 16 maio 2019.
http://repositorio.unb.br/handle/10482/33450
http://dx.doi.org/10.21577/0103-5053.20170114
identifier_str_mv COSTA, Maísa B. et al. Synthesis and expansion of bicyclic enol ether: a probable precursor for the synthesis of macrolide (±)-pyrenophorin. Journal of the Brazilian Chemical Society, São Paulo, v. 29, n. 1, p. 74-78, jan. 2018. DOI: http://dx.doi.org/10.21577/0103-5053.20170114. Disponível em: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100074&lng=en&nrm=iso. Acesso em: 16 maio 2019.
url http://repositorio.unb.br/handle/10482/33450
http://dx.doi.org/10.21577/0103-5053.20170114
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
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 reponame:Repositório Institucional da UnB
instname:Universidade de Brasília (UnB)
instacron:UNB
instname_str Universidade de Brasília (UnB)
instacron_str UNB
institution UNB
reponame_str Repositório Institucional da UnB
collection Repositório Institucional da UnB
repository.name.fl_str_mv Repositório Institucional da UnB - Universidade de Brasília (UnB)
repository.mail.fl_str_mv repositorio@unb.br
_version_ 1814508353353678848

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