2014
Total synthesis and isolation of citrinalin and cyclopiamine congeners
Mercado-Marin EV, Garcia-Reynaga P, Romminger S, Pimenta EF, Romney DK, Lodewyk MW, Williams DE, Andersen RJ, Miller SJ, Tantillo DJ, Berlinck RG, Sarpong R. Total synthesis and isolation of citrinalin and cyclopiamine congeners. Nature 2014, 509: 318-324. PMID: 24828190, PMCID: PMC4117207, DOI: 10.1038/nature13273.Peer-Reviewed Original ResearchMeSH KeywordsAlkaloidsBiological ProductsChemistry Techniques, SyntheticIndole AlkaloidsIndolizidinesMolecular StructureNitrogenOxidation-ReductionOxygenStereoisomerismConceptsNitrogen atomsChemical synthesisMultiple nitrogen atomsBasic nitrogen atomTotal synthesisFunctional groupsNatural productsSelective introductionTarget moleculesSuch compoundsChemical connectionsSynthesisAtomsBiogenetic precursorBasicityCompoundsMoleculesBroad rangePrecursorsAlkaloidsPresenceCongenersProducts
2013
Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors
Gould ND, Allen C, Nam BC, Schepartz A, Miller SJ. Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors. Carbohydrate Research 2013, 382: 36-42. PMID: 24177201, DOI: 10.1016/j.carres.2013.09.011.Peer-Reviewed Original ResearchMeSH KeywordsAcetamidesBiomimeticsCatalysisChemistry Techniques, SyntheticChloroacetatesGlycosylationKineticsLewis AcidsMagnesiumConceptsLewis acidGlycosylation reactionsCombined Lewis acidControl reactionsSubsequent kinetic studiesCatalytic systemBiomimetic conditionsCarboxylic acidsGlycosyl donorsIrreversible reactionKinetic studiesReactionAcid actsCatalytic componentAcidActive enzymeCarbohydrate-active enzymesCatalystProof of principleReactivityDonorsGlycosylStructureAn efficient chemical synthesis of carboxylate-isostere analogs of daptomycin
Yoganathan S, Yin N, He Y, Mesleh MF, Gu YG, Miller SJ. An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin. Organic & Biomolecular Chemistry 2013, 11: 4680-4685. PMID: 23752953, PMCID: PMC4033608, DOI: 10.1039/c3ob40924d.Peer-Reviewed Original ResearchConceptsSide-chain carboxylic acid groupsDirect synthetic procedureEfficient chemical synthesisCarboxylic acid groupsCarboxylic acid moietySynthetic procedureChemical synthesisBackbone cyclizationEsterification protocolAcid groupsAcid moietyCarboxylate isosteresBackbone amidesSynthesisAspartic acidGlutamic acidAcidMoietyAnaloguesCyclizationEfficient methodIsosteresAmidesHerein