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A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[ b ]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents

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Flynn, Bernard; Verdier-Pinard, Pascal; Hamel, Ernest

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Flexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o-ethynylpnenyl sulfides which react with iodine to give 3-iodobenzo[b]thiophenes in a 5-endo-dig iodocyclization. These iodides can be further elaborated using palladium-mediated coupling and/or metalation techniques. This method has been applied to the synthesis of some...[Show more]

dc.contributor.authorFlynn, Bernard
dc.contributor.authorVerdier-Pinard, Pascal
dc.contributor.authorHamel, Ernest
dc.date.accessioned2015-12-10T23:24:41Z
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/1885/67303
dc.description.abstractFlexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o-ethynylpnenyl sulfides which react with iodine to give 3-iodobenzo[b]thiophenes in a 5-endo-dig iodocyclization. These iodides can be further elaborated using palladium-mediated coupling and/or metalation techniques. This method has been applied to the synthesis of some novel tubulin binding agents.
dc.publisherAmerican Chemical Society
dc.sourceOrganic Letters
dc.subjectKeywords: antineoplastic agent; benzothiophene; colchicine; palladium; thiophene derivative; tubulin; article; catalysis; cell culture; chemistry; human; protein binding; structure activity relation; synthesis; Antineoplastic Agents; Catalysis; Colchicine; Humans;
dc.titleA Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[ b ]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents
dc.typeJournal article
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.citationvolume3
dc.date.issued2001
local.identifier.absfor039904 - Organometallic Chemistry
local.identifier.ariespublicationMigratedxPub1433
local.type.statusPublished Version
local.contributor.affiliationFlynn, Bernard, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationVerdier-Pinard, Pascal, National Institutes of Health
local.contributor.affiliationHamel, Ernest, National Institutes of Health
local.description.embargo2037-12-31
local.bibliographicCitation.issue5
local.bibliographicCitation.startpage651
local.bibliographicCitation.lastpage654
local.identifier.doi10.1021/ol0067179
dc.date.updated2015-12-10T10:49:21Z
local.identifier.scopusID2-s2.0-0035826341
CollectionsANU Research Publications

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