Studies on Tetrahydroisoquinolines. VI. Synthesis of (±)-Thaliporphine and (±)-Glaucine via a p-Quinol Acetate

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Acid-catalyzed (conc. sulfuric acid-acetic anhydride) reaction of p-quinol acetate (IIb) prepared by lead tetraacetate oxidation of (±)-codamine (Ic) was found to give (±)-4-acetoxy-O-acetylthaliporphine (VII) and (±)-O-acetylthaliporphine (IX), respectively. Both VII and IX were converted into (±)-thaliporphine (IV), whose methylation gave (±)-glaucine (X).