Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenones

Detalhes bibliográficos
Autor(a) principal: Mahajan,Jaswant Rai
Data de Publicação: 1997
Outros Autores: Resck,Inês Sabioni
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=S0103-50531997000600007
Resumo: Medium to macrocyclic acetylenic lactones 15a-e 6-decyn-9-olide (15a), 7-undecyn-10-olide (15b), 8-dodecyn-11-olide (15c), 12-hexadecyn-15-olide (15d), and 5-decyn-9-olide (15e) were prepared from oxabicycloalkenones 7a-d and 2, respectively, by the ring expansion of their tosylhydrazones 16a-e, carried out by reaction with N-bromosuccinimide, under strictly controlled conditions. Complete hydrogenation (Pd-C, H2) of the triple bond gave the racemic saturated lactones: 9-decanolide (phoracantholide I, 6, from 15a and 15e), 10-undecanolide, 11-dodecanolide (dihydrorecifeiolide), and 15-hexadecanolide. The attempts at the conversion of dihydropyrones 7a,d into the respective acetylenic lactones 15a,d, via chlorohydrins 8a,d and/or chloroketolactones 9a,d, were only partially successful.
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spelling Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenonesacetylenic lactoneschloroketolactoneschlorohydrinsring expansiontosylhydrazonesfragmentation reactionMedium to macrocyclic acetylenic lactones 15a-e 6-decyn-9-olide (15a), 7-undecyn-10-olide (15b), 8-dodecyn-11-olide (15c), 12-hexadecyn-15-olide (15d), and 5-decyn-9-olide (15e) were prepared from oxabicycloalkenones 7a-d and 2, respectively, by the ring expansion of their tosylhydrazones 16a-e, carried out by reaction with N-bromosuccinimide, under strictly controlled conditions. Complete hydrogenation (Pd-C, H2) of the triple bond gave the racemic saturated lactones: 9-decanolide (phoracantholide I, 6, from 15a and 15e), 10-undecanolide, 11-dodecanolide (dihydrorecifeiolide), and 15-hexadecanolide. The attempts at the conversion of dihydropyrones 7a,d into the respective acetylenic lactones 15a,d, via chlorohydrins 8a,d and/or chloroketolactones 9a,d, were only partially successful.Sociedade Brasileira de Química1997-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531997000600007Journal of the Brazilian Chemical Society v.8 n.6 1997reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50531997000600007info:eu-repo/semantics/openAccessMahajan,Jaswant RaiResck,Inês Sabionieng2010-07-23T00:00:00Zoai:scielo:S0103-50531997000600007Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2010-07-23T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenones
title Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenones
spellingShingle Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenones
Mahajan,Jaswant Rai
acetylenic lactones
chloroketolactones
chlorohydrins
ring expansion
tosylhydrazones
fragmentation reaction
title_short Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenones
title_full Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenones
title_fullStr Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenones
title_full_unstemmed Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenones
title_sort Synthesis of medium ring and macrocyclic acetylenic lactones by the ring expansion of oxabicycloalkenones
author Mahajan,Jaswant Rai
author_facet Mahajan,Jaswant Rai
Resck,Inês Sabioni
author_role author
author2 Resck,Inês Sabioni
author2_role author
dc.contributor.author.fl_str_mv Mahajan,Jaswant Rai
Resck,Inês Sabioni
dc.subject.por.fl_str_mv acetylenic lactones
chloroketolactones
chlorohydrins
ring expansion
tosylhydrazones
fragmentation reaction
topic acetylenic lactones
chloroketolactones
chlorohydrins
ring expansion
tosylhydrazones
fragmentation reaction
description Medium to macrocyclic acetylenic lactones 15a-e 6-decyn-9-olide (15a), 7-undecyn-10-olide (15b), 8-dodecyn-11-olide (15c), 12-hexadecyn-15-olide (15d), and 5-decyn-9-olide (15e) were prepared from oxabicycloalkenones 7a-d and 2, respectively, by the ring expansion of their tosylhydrazones 16a-e, carried out by reaction with N-bromosuccinimide, under strictly controlled conditions. Complete hydrogenation (Pd-C, H2) of the triple bond gave the racemic saturated lactones: 9-decanolide (phoracantholide I, 6, from 15a and 15e), 10-undecanolide, 11-dodecanolide (dihydrorecifeiolide), and 15-hexadecanolide. The attempts at the conversion of dihydropyrones 7a,d into the respective acetylenic lactones 15a,d, via chlorohydrins 8a,d and/or chloroketolactones 9a,d, were only partially successful.
publishDate 1997
dc.date.none.fl_str_mv 1997-01-01
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=S0103-50531997000600007
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531997000600007
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50531997000600007
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.8 n.6 1997
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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