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
Description
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.author | Flynn, Bernard | |
---|---|---|
dc.contributor.author | Verdier-Pinard, Pascal | |
dc.contributor.author | Hamel, Ernest | |
dc.date.accessioned | 2015-12-10T23:24:41Z | |
dc.identifier.issn | 1523-7060 | |
dc.identifier.uri | http://hdl.handle.net/1885/67303 | |
dc.description.abstract | 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 novel tubulin binding agents. | |
dc.publisher | American Chemical Society | |
dc.source | Organic Letters | |
dc.subject | Keywords: 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.title | A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[ b ]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents | |
dc.type | Journal article | |
local.description.notes | Imported from ARIES | |
local.description.refereed | Yes | |
local.identifier.citationvolume | 3 | |
dc.date.issued | 2001 | |
local.identifier.absfor | 039904 - Organometallic Chemistry | |
local.identifier.ariespublication | MigratedxPub1433 | |
local.type.status | Published Version | |
local.contributor.affiliation | Flynn, Bernard, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Verdier-Pinard, Pascal, National Institutes of Health | |
local.contributor.affiliation | Hamel, Ernest, National Institutes of Health | |
local.description.embargo | 2037-12-31 | |
local.bibliographicCitation.issue | 5 | |
local.bibliographicCitation.startpage | 651 | |
local.bibliographicCitation.lastpage | 654 | |
local.identifier.doi | 10.1021/ol0067179 | |
dc.date.updated | 2015-12-10T10:49:21Z | |
local.identifier.scopusID | 2-s2.0-0035826341 | |
Collections | ANU Research Publications |
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