2015
Synthesis of ent‐Ketorfanol via a C–H Alkenylation/Torquoselective 6π Electrocyclization Cascade
Phillips E, Mesganaw T, Patel A, Duttwyler S, Mercado B, Houk K, Ellman J. Synthesis of ent‐Ketorfanol via a C–H Alkenylation/Torquoselective 6π Electrocyclization Cascade. Angewandte Chemie 2015, 127: 12212-12216. DOI: 10.1002/ange.201505604.Peer-Reviewed Original ResearchElectrocyclization cascadeIntramolecular Friedel-Crafts alkylationFriedel–Crafts alkylationAvailable precursorsAsymmetric synthesisObserved selectivityKey intermediateKetone functionalityHigh torquoselectivityAcid-catalyzed rearrangementVicinal diolsFused bicyclicComputational studyConformational effectsRh ISingle stepFinal ringSynthesisSynthesis of ent‐Ketorfanol via a C–H Alkenylation/Torquoselective 6π Electrocyclization Cascade
Phillips EM, Mesganaw T, Patel A, Duttwyler S, Mercado BQ, Houk KN, Ellman JA. Synthesis of ent‐Ketorfanol via a C–H Alkenylation/Torquoselective 6π Electrocyclization Cascade. Angewandte Chemie International Edition 2015, 54: 12044-12048. PMID: 26385263, PMCID: PMC4676713, DOI: 10.1002/anie.201505604.Peer-Reviewed Original ResearchConceptsElectrocyclization cascadeIntramolecular Friedel-Crafts alkylationFriedel–Crafts alkylationAvailable precursorsAsymmetric synthesisObserved selectivityKey intermediateKetone functionalityHigh torquoselectivityAcid-catalyzed rearrangementVicinal diolsFused bicyclicComputational studyConformational effectsSingle stepFinal ringSynthesis
2014
Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C–H Functionalization Sequences
Mesganaw T, Ellman JA. Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C–H Functionalization Sequences. Organic Process Research & Development 2014, 18: 1097-1104. PMID: 25288871, PMCID: PMC4183667, DOI: 10.1021/op500224x.Peer-Reviewed Original ResearchCascade reactionVersatile synthetic intermediatesAddition of electrophilesH functionalization sequenceSynthetic intermediatesDihydropyridine productsAvailable precursorsConvergent synthesisDihydropyridine intermediatesFunctionalization sequenceBicyclic structureCatalyzed CReaction sequencePiperidine productsExcellent diastereoselectivityUseful yieldsSubsequent additionReactionIntermediatesThermodynamic conditionsFurther elaborationPrecatalystIminiumIsoquinuclidinesNucleophiles
1999
General Solid-Phase Method for the Preparation of Mechanism-Based Cysteine Protease Inhibitors
Lee A, Huang L, Ellman J. General Solid-Phase Method for the Preparation of Mechanism-Based Cysteine Protease Inhibitors. Journal Of The American Chemical Society 1999, 121: 9907-9914. DOI: 10.1021/ja992009a.Peer-Reviewed Original ResearchNucleophilic displacementGeneral solid-phase methodExpedient solid-phase synthesisSolid-phase synthesisSolid-phase methodFirst general methodKetone productsAvailable precursorsSolid supportΑ-stereocenterKetone carbonylCysteine protease inhibitorsOverall yieldFurther transformationDiverse functionalitiesSynthesis approachHydrazones 8ThiolatesCarboxylateChloromethyl ketoneCarbonylGeneral methodKetonesAminesMercaptomethyl
1998
General Solid-Phase Synthesis Approach To Prepare Mechanism-Based Aspartyl Protease Inhibitor Libraries. Identification of Potent Cathepsin D Inhibitors
Lee C, Kick E, Ellman J. General Solid-Phase Synthesis Approach To Prepare Mechanism-Based Aspartyl Protease Inhibitor Libraries. Identification of Potent Cathepsin D Inhibitors. Journal Of The American Chemical Society 1998, 120: 9735-9747. DOI: 10.1021/ja981812m.Peer-Reviewed Original ResearchSolid-phase synthesis approachSynthesis approachSolid-phase synthesisExpedient solid-phase synthesisProtease inhibitor libraryAvailable precursorsSynthesis sequenceSeparate compoundsStereoselective reductionPotent small molecule inhibitorsSmall molecule inhibitorsOverall yieldDiverse functionalitiesEnzyme classesProtease targetsMolecule inhibitorsGeneral design principlesAspartyl protease inhibitorsCathepsin D inhibitorInhibitor libraryPure inhibitorGeneral methodBondsAmino acidsCompounds
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