Studies on Tetrahydroisoquinolines. IX. The Synthesis of (±)-Domesticine and a Related (±)-Homoaporphine via p-Quinol Acetates

Abstract

Acid (conc. H₂SO₄-Ac₂O) treatment of the p-quinol acetate derived from (±)-1, 2, 3, 4-tetrahydro-7-hydroxy-6-methoxy-2-methyl-1-(3', 4'-methylenedioxy-benzyl or -phenethyl)-isoquinoline (VIII or IX) gave the corresponding 1-monoacetoxy-and 1, 4-diacetoxy-aporphine (XIX, XXa, and XXb) or-homoaporphine (XXIII and XXIV), respectively. Hydrolysis of XIX afforded (±)-domesticine (VI).