Formation and Reactions of the Cyclic Tautomers of Tryptophans and Tryptamines. VII. Hydroxylation of Tryptophans and Tryptamines

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The 5-hydroxytryptophan derivative 12 was prepared in 60% yield from the tryptophan derivative 8 by selective oxidation of the cyclic tautomer 9 with Fremy's salt or Pb (OAc)_4-CF_3COOH to the p-quinoneimine 10,followed by reduction and ring-opening. By analogous oxidation, serotonin was prepared from tryptamine. On the other hand, the oxidation of the N_a-acetyl-cyclic tautomers (16 and 22) with Pb (OAc)_4-CF_3COOH followed by methylation gave the 5-and 6-methoxy derivatives (17,18,23,and 24) in 20-40% yields. These compounds were readily converted to the 5-and 6-methoxytryptophan derivatives (20,21) by acid treatment. These methods are the first practical hydroxylation procedures to be reported for tryptophans.
社団法人日本薬学会の論文
1984-07-25