A novel ring cleavage and recyclization of N-cyanomethyl-1,2,3,4-tetrahydroisoquinolinium methiodides: A biomimetic synthesis of litebamine

Article abstract of DOI:10.1016/0040-4020(95)00614-E

Treatment of N-cyanomethyl-6-hydroxy-1,2,3,4-tetrahydroisoquinolinium methiodide (1) with NaOMe in MeOH caused C₁-N fission and simultaneous recyclization to give 8-hydroxy-5-methoxymethyl-1,2,3,4-tetrahydroisoquinoline (2). By using of the rea