Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)

Detalhes bibliográficos
Autor(a) principal: Dias,Luiz Carlos
Data de Publicação: 2013
Outros Autores: Farina,Lui Strambi, Ferreira,Marco Antonio Barbosa
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=S0103-50532013000200003
Resumo: A short and efficient stereoselective total synthesis of CMI-977 (LDP-977), a potent and orally active anti-asthmatic compound, was developed. The key steps involve a highly diastereoselective Mukaiyama oxidative cyclization, which provides the trans-THF (tetrahydrofuran) unit and a Seyferth-Gilbert homologation to construct the triple bond in the target molecule. The synthesis of the key chiral building block was performed using Jacobsen hydrolytic kinetic resolution.
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spelling Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)total synthesisCMI-977Mukaiyama oxidative cyclizationJacobsen hydrolytic kinetic resolutionSeyferth-Gilbert homologationA short and efficient stereoselective total synthesis of CMI-977 (LDP-977), a potent and orally active anti-asthmatic compound, was developed. The key steps involve a highly diastereoselective Mukaiyama oxidative cyclization, which provides the trans-THF (tetrahydrofuran) unit and a Seyferth-Gilbert homologation to construct the triple bond in the target molecule. The synthesis of the key chiral building block was performed using Jacobsen hydrolytic kinetic resolution.Sociedade Brasileira de Química2013-02-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000200003Journal of the Brazilian Chemical Society v.24 n.2 2013reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20130024info:eu-repo/semantics/openAccessDias,Luiz CarlosFarina,Lui StrambiFerreira,Marco Antonio Barbosaeng2013-05-20T00:00:00Zoai:scielo:S0103-50532013000200003Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2013-05-20T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)
title Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)
spellingShingle Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)
Dias,Luiz Carlos
total synthesis
CMI-977
Mukaiyama oxidative cyclization
Jacobsen hydrolytic kinetic resolution
Seyferth-Gilbert homologation
title_short Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)
title_full Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)
title_fullStr Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)
title_full_unstemmed Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)
title_sort Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)
author Dias,Luiz Carlos
author_facet Dias,Luiz Carlos
Farina,Lui Strambi
Ferreira,Marco Antonio Barbosa
author_role author
author2 Farina,Lui Strambi
Ferreira,Marco Antonio Barbosa
author2_role author
author
dc.contributor.author.fl_str_mv Dias,Luiz Carlos
Farina,Lui Strambi
Ferreira,Marco Antonio Barbosa
dc.subject.por.fl_str_mv total synthesis
CMI-977
Mukaiyama oxidative cyclization
Jacobsen hydrolytic kinetic resolution
Seyferth-Gilbert homologation
topic total synthesis
CMI-977
Mukaiyama oxidative cyclization
Jacobsen hydrolytic kinetic resolution
Seyferth-Gilbert homologation
description A short and efficient stereoselective total synthesis of CMI-977 (LDP-977), a potent and orally active anti-asthmatic compound, was developed. The key steps involve a highly diastereoselective Mukaiyama oxidative cyclization, which provides the trans-THF (tetrahydrofuran) unit and a Seyferth-Gilbert homologation to construct the triple bond in the target molecule. The synthesis of the key chiral building block was performed using Jacobsen hydrolytic kinetic resolution.
publishDate 2013
dc.date.none.fl_str_mv 2013-02-01
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=S0103-50532013000200003
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000200003
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20130024
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.24 n.2 2013
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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