Synthesis of saulatine

Article abstract of DOI:10.1002/jhet.5570300541

A study directed toward the synthesis of saulatine (5,8,9,14a-tetrahydro- 3,4,11,12-tetramethoxy-isoquino[1,2-b]benzazepine-6,14-dione) is described. The successful synthetic route consists of three steps starting with 3,4- dimethoxyphenethylamine and 2-bromo-(3,4-dimethoxy-2- ethoxycarbomethylphenyl)-acetate. It was found that the methoxy moieties present on the aromatic rings prohibit the use of the intramolecular Friedel- Crafts reaction with a Lewis acid catalyst for ring construction because of their demethylation tendency under the reaction conditions.