title: Synthesis of deuterated gamma-lactones for use in stable isotope dilution assays.
abstract: Two syntheses of deuterated gamma-lactones for use as internal standards in stable isotope dilution assays (SIDA) were developed. [2,2,3,3-2H4]-gamma-Octa-, -gamma-deca-, and -gamma-dodecalactones with >89% deuterium incorporation were prepared in 27, 17, and 19% overall yields, respectively, by the reduction of a doubly protected hydroxypropiolic acid with deuterium gas. [3,3,4-2H3]-gamma-Octa- and -gamma-dodecalactones were prepared in 6 and 23% yields with >92% deuterium incorporation by the free radical addition of 2-iodoacetamide to [1,1,2-2H3]-1-hexene and [1,1,2-2H3]-1-decene, respectively. Reaction yields were highly dependent upon the purity of the 1-alkene starting material. The deuterated gamma-lactones were evaluated as internal standards for SIDA.
authors.affiliation: The Horticulture and Food Research Institute of New Zealand Ltd., Private Bag 11030, Palmerston North, New Zealand.
authors.forename: Jo-Anna
authors.initials: JA
authors.lastname: Hislop
authors.forename: Martin B
authors.initials: MB
authors.lastname: Hunt
authors.forename: Simon
authors.initials: S
authors.lastname: Fielder
authors.forename: Daryl D
authors.initials: DD
authors.lastname: Rowan
mesh_terms: D003903:Deuterium; D007201:Indicator Dilution Techniques; D007553:Isotope Labeling; D007783:Lactones / Q000737:chemistry*
chemical_list: D007783:Lactones; D003903:Deuterium