AN ECONOMICAL SYNTHESIS OF AILANTHOIDOL

摘要

PURPOSE: A method for synthesizing ailanthoidol is provided to induce Sonogashira coupling without introduction of a protection group and to enhance efficiency. CONSTITUTION: A method for synthesizing ailanthoidol of chemical formula 6 comprises: a step of reacting vanillin of chemical formula 1 and silver sulfate by iodination to prepare 4-hydroxy-3-iodo-5-methoxybenzaldehyde of chemical formula 2; a step of performing Sonogashira coupling and cyclization of the compound of chemical formula 2 with an acethylene derivative to prepare 2-(4-benzyloxy-3-methoxyphenyl)-7-methoxybenzofuran-5-carbaldehyde of chemical formula 3; a step of performing Wittig reaction of the compound of chemical formula 3 with carbethoxymethylene triphenylphosphorane to prepare 2-(4-benzyloxy-3-methoxyphenyl)-5-(carbethoxyethenyl)-7-methoxybenzofuran of chemical formula 4; a step of performing debenzylation of the compound of chemical formula 4 using TiCl_4 to prepare 2-(4-hydroxy-3-methoxyphenyl)-5-(carbethoxyethenyl)-7-methoxybenzofuran of chemical formula 5; and a step of reducing the compound of chemical formula 5 using DIBAL-H to prepare a compound of chemical formula 6.