2017
Enantioselective Intermolecular C–O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst
Chinn AJ, Kim B, Kwon Y, Miller SJ. Enantioselective Intermolecular C–O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst. Journal Of The American Chemical Society 2017, 139: 18107-18114. PMID: 29116792, PMCID: PMC5738244, DOI: 10.1021/jacs.7b11197.Peer-Reviewed Original ResearchConceptsComplex molecular settingsO bond formationPeptide-based ligandsCross-coupling reactionsPhenolic hydroxyl groupsIntermolecular CuIntermolecular CChemoselective reactionTBu groupBond formationAppreciable selectivityReactive sitesPhenolic nucleophilesHydroxyl groupsSteric perturbationsMaximum enantioselectivitySecond reactive siteMolecular settingNucleophilesDesymmetrizationUncommon levelReactionSubstrateCatalystChemistry
2013
Chemical Tailoring of Teicoplanin with Site-Selective Reactions
Pathak TP, Miller SJ. Chemical Tailoring of Teicoplanin with Site-Selective Reactions. Journal Of The American Chemical Society 2013, 135: 8415-8422. PMID: 23692563, PMCID: PMC3800266, DOI: 10.1021/ja4038998.Peer-Reviewed Original ResearchConceptsNew compoundsSelective cross-coupling reactionsChemical reactionsOrthogonal chemical reactionsSite-selective reactionsTotal chemical synthesisCross-coupling reactionsNatural product derivativesTwo-step accessChemical tailoringChemical synthesisProduct derivativesChemical modificationPoor selectivityAntibacterial propertiesAntibiotic teicoplaninReactionChemical alterationImproved analoguesCompoundsUnmet challengeAnaloguesSelectivitySemisynthesisComplex structure