title: Animal carotenoids. 31. Structure elucidation of a sponge metabolite via mesylate elimination.
abstract: The structure of a sponge metabolite from Microciona prolifera, previously considered to be (6S)-2,3-didehydro- or 3,4-didehydro-gamma, chi-carotene, has been further studied. Attempted total synthesis of the 3,4-didehydro derivative provided the hitherto unknown gamma, chi-carotene, the synthesis of which is described. Hydrolysis of lutein methanesulfonate diester (dimesylate) gave elimination products possessing the 3,4-didehydro gamma end-group. 1H NMR data for this gamma end-group were identical with those for the sponge carotenoid. The mesylate elimination reaction described may mimic the metabolic formation of the 3,4-didehydro-gamma-carotenoid end-group. In connection with other investigations on functionalized carotenoids we further report the preparation of zeaxanthin and lutein mesylates and their base-catalyzed elimination reactions. SN2 type substitution reactions of zeaxanthin dimesylate with appropriate nucleophiles did not produce beta, beta-carotene, zeaxanthin diacetate or thiozeaxanthin.
authors.forename: H R
authors.initials: HR
authors.lastname: Sliwka
authors.forename: O W
authors.initials: OW
authors.lastname: Nøkleby
authors.forename: S
authors.initials: S
authors.lastname: Liaaen-Jensen
mesh_terms: D000818:Animals; D002338:Carotenoids / Q000032:analysis* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000032:analysis; D008968:Molecular Conformation; D011161:Porifera / Q000378:metabolism*
chemical_list: D008698:Mesylates; D002338:Carotenoids