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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.

acta chemica scandinavica/acta chemica scandinavica. b, organic chemistry and biochemistry/acta chemica scandinavica. a, physical and inorganic chemistry/acta chemica scandinavica. series b. organic chemistry and biochemistry/acta chemica scandinavica. series a, physical and inorganic chemistry

Animal Carotenoids. 31. Structure Elucidation of a Sponge Metabolite via Mesylate Elimination.