title: The taumycin A macrocycle: asymmetric total synthesis and revision of relative stereochemistry.
abstract: The first asymmetric total synthesis and revision of the relative configuration of the 12-membered taumycin A macrocycle is described. Key to the success of this work was a novel α-keto ketene macrocyclization that provided an efficient means by which to access two diastereomers of the desired macrolide without the need to employ additional coupling agents or unnecessary oxidation state adjustments.
authors.affiliation: Department of Chemistry and Biochemistry, New Mexico State University , Las Cruces, New Mexico 88003, United States.
authors.forename: Justine N
authors.initials: JN
authors.lastname: deGruyter
authors.forename: William A
authors.initials: WA
authors.lastname: Maio
mesh_terms: D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D047630:Depsipeptides; D005030:Ethylenes; D007659:Ketones; D018942:Macrolides; C532773:taumycin A; C008223:ketene