4-メトキシオイダリンおよび関連化合物の合成

抄録

4-Methoxyeudalene was synthesized from p-methylanisole. 3-(2-Methoxy-5-methylbenzoyl) propionic acid (1) was converted to 5-methoxy-8-methyl-1, 2, 3, 4-tetrahydronaphthalene-1-one (3). Ethyl 5-methoxy-8-methyl-1-oxo-1, 2, 3, 4-tetrahydronaphthalene-2-carboxylate (5), which was obtained by condensation with ethyl oxalate followed by pyrolysis of (3), was isopropylated and then hydrolyzed to give 2-isopropyl-5-methoxy-8-methyl-1, 2, 3, 4-tetrahydronaphthalene-1-one (7a). 4-Methoxyeudalene (9a) was obtained by reduction followed by heating with sulfur of (7a). The demethylation of (9a) with HBr afforded 4-hydroxyeudalene along with a neutral substance. Similary, 1-methoxy-4, 6-dimethylnaphthalene (9b) and 1-methoxy-4-methylnaphthalene (9c) were obtained from (5) and (3), respectively.