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Article: Steps towards a practical synthesis of macrocyclic bisbenzylisoquinolines

TitleSteps towards a practical synthesis of macrocyclic bisbenzylisoquinolines
Authors
Issue Date2005
Citation
Journal Of Heterocyclic Chemistry, 2005, v. 42 n. 4, p. 647-659 How to Cite?
AbstractThere are more than 400-reported bisbenzylisoquinoline alkaloids, many with interesting biological activity, but the reported syntheses are long and low yielding. As a result, there have been no systematic attempts at exploitation of the potential therapeutic applications. The concept of a sulfur 'stitch', restricting the conformational freedom of intermediates in the synthesis, will potentially allow analogues of the natural products to be prepared using relatively efficient routes. The synthesis of intermediate sulfur heterocycles is reported, based on 2,8-dimethylphenoxathiin, leading via 2,8-bis(bromomethyl) phenoxathiin-10,10-dioxide to a synthesis of 3,4,8,9-tetrahydro-13-oxa-6-thia-2, 10-diazapentacene, a key potential intermediate on the route to a variety of macrocyclic bisbenzylisoquinolines.
Persistent Identifierhttp://hdl.handle.net/10722/171331
ISSN
2015 Impact Factor: 0.685
2015 SCImago Journal Rankings: 0.245
References

 

DC FieldValueLanguage
dc.contributor.authorAlHiari, YMen_US
dc.contributor.authorBennett, SJen_US
dc.contributor.authorCox, Ben_US
dc.contributor.authorDavies, RJen_US
dc.contributor.authorKhalaf, AIen_US
dc.contributor.authorWaigh, RDen_US
dc.contributor.authorWorsley, AJen_US
dc.date.accessioned2012-10-30T06:13:24Z-
dc.date.available2012-10-30T06:13:24Z-
dc.date.issued2005en_US
dc.identifier.citationJournal Of Heterocyclic Chemistry, 2005, v. 42 n. 4, p. 647-659en_US
dc.identifier.issn0022-152Xen_US
dc.identifier.urihttp://hdl.handle.net/10722/171331-
dc.description.abstractThere are more than 400-reported bisbenzylisoquinoline alkaloids, many with interesting biological activity, but the reported syntheses are long and low yielding. As a result, there have been no systematic attempts at exploitation of the potential therapeutic applications. The concept of a sulfur 'stitch', restricting the conformational freedom of intermediates in the synthesis, will potentially allow analogues of the natural products to be prepared using relatively efficient routes. The synthesis of intermediate sulfur heterocycles is reported, based on 2,8-dimethylphenoxathiin, leading via 2,8-bis(bromomethyl) phenoxathiin-10,10-dioxide to a synthesis of 3,4,8,9-tetrahydro-13-oxa-6-thia-2, 10-diazapentacene, a key potential intermediate on the route to a variety of macrocyclic bisbenzylisoquinolines.en_US
dc.languageengen_US
dc.relation.ispartofJournal of Heterocyclic Chemistryen_US
dc.titleSteps towards a practical synthesis of macrocyclic bisbenzylisoquinolinesen_US
dc.typeArticleen_US
dc.identifier.emailWorsley, AJ:alanwor@hku.hken_US
dc.identifier.authorityWorsley, AJ=rp01395en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.scopuseid_2-s2.0-19644390052en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-19644390052&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume42en_US
dc.identifier.issue4en_US
dc.identifier.spage647en_US
dc.identifier.epage659en_US
dc.identifier.scopusauthoridAlHiari, YM=11941066300en_US
dc.identifier.scopusauthoridBennett, SJ=7403105617en_US
dc.identifier.scopusauthoridCox, B=7403198728en_US
dc.identifier.scopusauthoridDavies, RJ=7404392476en_US
dc.identifier.scopusauthoridKhalaf, AI=7006799960en_US
dc.identifier.scopusauthoridWaigh, RD=7003560125en_US
dc.identifier.scopusauthoridWorsley, AJ=16445153200en_US

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