The Synthesis of C-13 Labeled Vitamin E, [12'a, 13'-^<13>C] all-rac-α-Tocopherol

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[12'a, 13'-^<13>C] all-rac-α-Tocopherol (1) was synthesized from [1,3-^<13>C] acetone. The condensation of 6-methoxymethoxy-2,5,7,8-tetramethyl-2-[(E)-4-methyl-5-(thiazolin-2-yl) thio-3-penten-1-yl] chroman (8) with [7a, 8-^<13>C] geranyl bromide (7), which was prepared by the coupling of (E)-(6-benzoyloxy-4-methyl-4-hexen-1-yl) triphenylphosphonium bromide (5) with [1,3-^<13>C] acetone, followed by bromination, afforded 6-methoxymethoxy-2,5,7,8-tetramethyl-2-[12a, 13-^<13>C] (3E, 7E, 11E) 4,8,12-trimethyl-5-(thiazolin-2-yl) thio-3,7,11-tridecatrien-1-yl] chroman (9). After desulfurization and reduction of 9,the reaction product was converted to [12'a, 13'-^<13>C] all-rac-α-tocopherol (1) by the use of methanolic hydrogen chloride. The overall yield of 1 was 33% on the basis of [1,3-^<13>C] acetone.
社団法人日本薬学会の論文
1985-03-25