2017
Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids
Key HM, Miller SJ. Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids. Journal Of The American Chemical Society 2017, 139: 15460-15466. PMID: 28975793, PMCID: PMC5736372, DOI: 10.1021/jacs.7b08775.Peer-Reviewed Original ResearchConceptsComplex moleculesSite-selective catalysisComplex molecular settingsComplex natural productsSite-selective modificationPotassium saltNew analoguesApplication of RhFunctional group toleranceEnantioselective catalysisSelective functionalizationCatalyst systemAnalogous reactionStereoselective functionalizationEnantioselective synthesisGroup toleranceNatural productsActive moleculesPotent antibacterial propertiesDehydroalanine residuesBiological testingAmino estersHigh stereoselectivityAntibacterial propertiesMolecular settingApplications of Nonenzymatic Catalysts to the Alteration of Natural Products
Shugrue CR, Miller SJ. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products. Chemical Reviews 2017, 117: 11894-11951. PMID: 28580785, PMCID: PMC5742423, DOI: 10.1021/acs.chemrev.7b00022.Peer-Reviewed Original ResearchConceptsNatural productsNonenzymatic catalystsComplex molecular scaffoldsComplex natural productsH bond functionalizationC bond formationNatural product scaffoldsLate-stage functionalizationNatural product derivativesSynthesis of analoguesChemical functionalityMedicinal chemistryBond functionalizationElectrophilic reagentsOlefin functionalizationSelectivity challengesBiological activity assaysBond formationEnzymatic catalystsProduct derivativesMolecular scaffoldsCatalystComplex moleculesChemical remodelingSmall molecules
2014
Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones
Romney DK, Colvin SM, Miller SJ. Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones. Journal Of The American Chemical Society 2014, 136: 14019-14022. PMID: 25250713, PMCID: PMC4195385, DOI: 10.1021/ja508757g.Peer-Reviewed Original ResearchConceptsBaeyer-Villiger oxidationPeptide-based catalystsHydrogen bonding interactionsTypes of selectivityParallel kinetic resolutionCatalyst controlFunctionalized KetonesCyclic ketonesFunctional groupsNatural productsComplex moleculesKinetic resolutionAsymmetric processEnantioselectivityRegioKetonesOxidationBroad utilityCatalystCatalysisSelectivityAmidesSynthesisMoleculesProducts
2012
Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation
Lichtor PA, Miller SJ. Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation. Nature Chemistry 2012, 4: 990-995. PMID: 23174978, PMCID: PMC3506257, DOI: 10.1038/nchem.1469.Peer-Reviewed Original ResearchConceptsPeptide-based catalystsPossible stereochemical outcomesNon-enzymatic catalystsSimilar functional groupsCatalytic functionalizationEnantioselective catalystsChemical synthesisCombinatorial synthesisOxidation catalystAsymmetric oxidationEnzymatic catalysisCatalystEnantioselective oxidationFunctional groupsComplex moleculesStereochemical outcomeEvolution of enzymesSame moleculeOxidationSelectivitySynthesisCombinatorial evolutionMoleculesExhibit siteOnly precedent