From ascorbigens to indolocarbazoles

New methods of L-ascorbic acid derivatization with the use of polyfunctiona l indole-3-cabinols are described. Reaction of beta-hydroxy-N-methyltryptam ine and L-ascorbic acid gave lactame derivatives; (indol-3-yl)glycolic and L-ascorbic acids produced 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl) Similarl y, 4-hydroxy-3-methoxyphenylglycolic and L-ascorbic acids yielded 2-hydroxy -3-(4-hydroxy-3-methoxyphenyl)-4-hydroxymethyl-cyclopen-2-enone. Properties of N-methoxyascorbigen (neoascorbigen) were investigated. Alkylation of L- ascorbic acid with polysubstituted pyrrolecarbinols led to pyrrole analogue s of ascorbigen. Acidic transformation of 3-formylindole and 1-methyl-3-for mylindole led to indolocarbazoles and triindolyhmethane derivatives. (C) 19 99 Elsevier Science S.A. All rights reserved.