{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Tollefson EJ"],"funding":["National Cancer Institute","NCI NIH HHS","University of California","National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["14951-8"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC4210078"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["136(42)"],"pubmed_abstract":["The stereospecific ring-opening of O-heterocycles to provide acyclic alcohols and carboxylic acids with controlled formation of a new C-C bond is reported. These reactions provide new methods for synthesis of acyclic polyketide analogs with complex stereochemical arrays. Stereoselective synthesis of the cyclic template is utilized to control relative configuration; subsequent stereospecific nickel-catalyzed ring-opening affords the acyclic product. Aryl-substituted tetrahydrofurans and tetrahydropyrans undergo nickel-catalyzed Kumada-type coupling with a range of Grignard reagents to furnish acyclic alcohols with high diastereoselectivity. Enantioenriched lactones undergo Negishi-type cross-coupling with dimethylzinc to afford enantioenriched carboxylic acids. Application in a two-step enantioselective synthesis of an anti-dyslipidemia agent is demonstrated."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Stereospecific cross-coupling reactions of aryl-substituted tetrahydrofurans, tetrahydropyrans, and lactones."],"pmcid":["PMC4210078"],"funding_grant_id":["R01GM100212","F31CA177212","R01 GM100212","F31 CA177212"],"pubmed_authors":["Tollefson EJ","Jarvo ER","Osborne CA","Dawson DD"],"additional_accession":[]},"is_claimable":false,"name":"Stereospecific cross-coupling reactions of aryl-substituted tetrahydrofurans, tetrahydropyrans, and lactones.","description":"The stereospecific ring-opening of O-heterocycles to provide acyclic alcohols and carboxylic acids with controlled formation of a new C-C bond is reported. These reactions provide new methods for synthesis of acyclic polyketide analogs with complex stereochemical arrays. Stereoselective synthesis of the cyclic template is utilized to control relative configuration; subsequent stereospecific nickel-catalyzed ring-opening affords the acyclic product. Aryl-substituted tetrahydrofurans and tetrahydropyrans undergo nickel-catalyzed Kumada-type coupling with a range of Grignard reagents to furnish acyclic alcohols with high diastereoselectivity. Enantioenriched lactones undergo Negishi-type cross-coupling with dimethylzinc to afford enantioenriched carboxylic acids. Application in a two-step enantioselective synthesis of an anti-dyslipidemia agent is demonstrated.","dates":{"release":"2014-01-01T00:00:00Z","publication":"2014 Oct","modification":"2025-04-22T21:09:01.975Z","creation":"2019-03-27T01:38:23Z"},"accession":"S-EPMC4210078","cross_references":{"pubmed":["25308512"],"doi":["10.1021/ja5076426"]}}