抄録
Total syntheses of (±)-galanthamine (I-A) and thebaine (III-A)-a formal total synthesis of morphine (IV)-are discussed. Thus, phenol oxidation of the amide (XVI) with K_3Fe(CN)_6 gave the enone (XVII) (40%), which was reduced with LiAlH_4 to afford (±)-galanthamine (I-A) and (±)-epigalanthamine (I-B). Pschorr reaction of the (-)-aminoisoquinoline (XXV-A) and (+)-aminoisoquinoline (XXV-B) gave salutaridine (II-A) and sinoacutine (II-B), respectively, former of which was reduced to salutaridinol (XXVII-A), followed by acid treatment to afford thebaine (III-A). This means a formal total synthesis of morphine (IV). Phenol oxidation of reticuline (XXIX) gave the dienone (XXXI), which was also obtained by Pschorr reaction of the aminoisoquinoline. This dienone was isolated from Corydalis pallida var. tenuis and named "pallidine (VII)" by us.
