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dc.contributor.authorAndler, Oliver
dc.contributor.authorKazmaier, Uli
dc.date.accessioned2022-04-25T11:34:37Z
dc.date.available2022-04-25T11:34:37Z
dc.date.issued2023-03-28
dc.date.submitted2022-02-28
dc.identifier.citationOliver Andler and Uli Kazmaier Organic Letters 2022 24 (13), 2541-2545 DOI: 10.1021/acs.orglett.2c00701en_US
dc.identifier.pmid35343704
dc.identifier.doi10.1021/acs.orglett.2c00701
dc.identifier.urihttp://hdl.handle.net/10033/623174
dc.descriptionThe Matteson homologation was found to be a versatile tool for the construction of the linear polyketide side chain of meliponamycin and related compounds in only four steps. The ester dienolate version of this reaction allowed the introduction of the unsaturated ester moiety in a highly stereoselective fashion. Boronate oxidation/deoxygenation and Sharpless dihydroxylation are additional key steps in the stereoselective construction of this highly functionalized tetrahydropyran ring system, which is characteristic of this substance classen_US
dc.description.abstractThe Matteson homologation was found to be a versatile tool for the construction of the linear polyketide side chain of meliponamycin and related compounds in only four steps. The ester dienolate version of this reaction allowed the introduction of the unsaturated ester moiety in a highly stereoselective fashion. Boronate oxidation/deoxygenation and Sharpless dihydroxylation are additional key steps in the stereoselective construction of this highly functionalized tetrahydropyran ring system, which is characteristic of this substance classen_US
dc.description.sponsorshipFinancial support from Saarland University and the DFG (grants: Ka 880/13-1; Bruker Neo 500-447298507) is gratefully acknowledged. We thank Christine Walt from Helmholtz Institute for Pharmaceutical Research Saarland (HIPS) for support with the mass pectrometryen_US
dc.language.isoenen_US
dc.publisherACS/ American Chemical Societyen_US
dc.rightsAttribution-ShareAlike 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-sa/4.0/*
dc.subjectSubstituents; Redox reactions; Organic compounds ; Pharmaceuticals; Metabolismen_US
dc.subject.meshEsters;en_US
dc.subject.meshStereoisomerismen_US
dc.titleStereoselective Synthesis of a Protected Side Chain of Meliponamycin A.en_US
dc.typeArticleen_US
dc.typeLetteren_US
dc.identifier.eissn1523-7052
dc.contributor.departmentOrganic Chemistry I, Saarland University, Campus Building C4.2, D-66123 Saarbrücken, GermanyHelmholtz Institute for Pharmaceutical Research Saarland (HIPS), Saarland University, Campus Building C8.1, D-66123 Saarbrücken, Germanyen_US
dc.identifier.journalOrganic lettersen_US
dc.source.volume24
dc.source.issue13
dc.source.beginpage2541
dc.source.endpage2545
dc.source.journaltitleOrganic letters
dc.source.countryUnited States


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