title: Enantioselective synthesis of isotopically labeled homocitric acid lactone.
abstract: A concise synthesis of homocitric acid lactone was developed to accommodate systematic placement of carbon isotopes (specifically (13)C) for detailed studies of this cofactor. This new route uses a chiral allylic alcohol, available in multigram quantities from enzymatic resolution, as a starting material, which transposes asymmetry through an Ireland-Claisen rearrangement.
authors.affiliation: Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States and Physical Biosciences Division, Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA 94720.
authors.forename: Jared T
authors.initials: JT
authors.lastname: Moore
authors.forename: Nadine V
authors.initials: NV
authors.lastname: Hanhan
authors.forename: Maximillian E
authors.initials: ME
authors.lastname: Mahoney
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Cramer
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw
mesh_terms: D002247:Carbon Isotopes / Q000737:chemistry*; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014233:Tricarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002247:Carbon Isotopes; D007783:Lactones; D014233:Tricarboxylic Acids; C028143:homocitric acid