PRODUCTION OF TETRAHYDRONAPHTHACENE DERIVATIVE

摘要

PURPOSE:To obtain the titled compound useful as a synthetic intermediate having remarkable carcinostatic activity, in one step and high yield under mild condition, by using a specific compound and phthaloyl dichloride as raw materials and reacting the materials in the presence of a Lewis acid catalyst. CONSTITUTION:The objective compound of formula III can be produced by reacting the compound of formula I [R<1> is acetyl or lower alkoxycarbonyl; R<2> is OR<3> (R<3> is H or OH-protecting group), NHCOR<4> (R<4> is lower alkyl or lower halogenoalkyl) or group of formula II (X is H or halogen)] with phthaloyl dichloride in a solvent such as dried dichloroethane in the presence of a Lewis acid such as AlCl3 at room temperature for 2-16hr. EFFECT:The objective compound can be produced in high optical purity on an industrial scale without causing racemization of the product. USE:A synthetic intermediate for 4-demethoxydaunomycin or 4-deme thoxyadriamycin which are anthracycline-type antibiotic substances of non-natu ral origin and having remarkable carcinostatic activity.