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dc.contributor.authorAli, Rameez
dc.contributor.authorAnugu, Sreenivasa
dc.contributor.authorChawla, Reena
dc.contributor.authorDemillo, Violeta G
dc.contributor.authorGoulinet-Mateo, Florian
dc.contributor.authorGyawali, Sagar
dc.contributor.authorHamal, Sunil
dc.contributor.authorJones, Dylan E
dc.contributor.authorLamprecht, Katrin
dc.contributor.authorLe, Truc
dc.contributor.authorLumangtad, Liezel A
dc.contributor.authorPflug, Nicholas C
dc.contributor.authorSama, Alekhya
dc.contributor.authorScarbrough, Emily D
dc.contributor.authorBell, Thomas W
dc.date.accessioned2019-06-24T18:31:40Z
dc.date.available2019-06-24T18:31:40Z
dc.date.issued2019-01-31
dc.identifier.citationACS Omega 2019, 4, 1254−1264en_US
dc.identifier.issn2470-1343
dc.identifier.pmid30729225
dc.identifier.doi10.1021/acsomega.8b02555
dc.identifier.urihttp://hdl.handle.net/10150/633018
dc.description.abstractMacrocyclic triamine disulfonamides can be synthesized by double Tsuji-Trost N-allylation reaction of open-chain disulfonamides with 2-alkylidene-1,3-propanediyl bis(carbonates). The previously used Atkins-Richman macrocyclization method generally gives lower yields and requires more tedious purification of the product. Solvent, palladium source, ligand, and concentration have all been varied to optimize the yields of two key 12-membered ring bioactive compounds, CADA and VGD020. The new approach tolerates a wide range of functional groups and gives highest yields for symmetrical compounds in which the acidities of the two sulfonamide groups are matched, although the yields of unsymmetrical compounds are still generally good. The method has also been extended to the synthesis of 11-membered rings, pyridine-fused macrocycles, and products bearing an ester or aryl substituent on the exocyclic double bond.en_US
dc.description.sponsorshipNIH [1R15 GM120659-01]en_US
dc.language.isoenen_US
dc.publisherAMER CHEMICAL SOCen_US
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/acsomega.8b02555en_US
dc.rightsCopyright © 2019 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.en_US
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/
dc.titleTsuji-Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triaminesen_US
dc.typeArticleen_US
dc.contributor.departmentUniv Arizona, BIO5 Insten_US
dc.identifier.journalACS OMEGAen_US
dc.description.noteOpen access journalen_US
dc.description.collectioninformationThis item from the UA Faculty Publications collection is made available by the University of Arizona with support from the University of Arizona Libraries. If you have questions, please contact us at repository@u.library.arizona.edu.en_US
dc.eprint.versionFinal published versionen_US
dc.source.journaltitleACS omega
refterms.dateFOA2019-06-24T18:31:40Z


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