Synthesis of morphine fragments spiro [benzofuran-3 (2H), 4′-piperidine] and octahydro-1H-benzofuro [3, 2-e] isoquinoline by intramolecular Heck reaction

CY Cheng, JP Liou, MJ Lee

Index: Cheng, Chen-Yu; Liou, Jing-Ping; Lee, Mei-Jing Tetrahedron Letters, 1997 , vol. 38, # 26 p. 4571 - 4574

Full Text: HTML

Citation Number: 33

Abstract

As a better alternative to radical cyclization, 5-(2-bromo-6-methoxyphenoxy)-2-methyl-1, 2, 3, 4, 5, 6, 7, 8-octahydroisoquinoline (2) and its 1-oxo analog 3 underwent Pd-catalyzed intramolecular cyclization to give the tetracyclic (ACNO) morphine fragments 5 and 6 respectively. 4-[(2′-Iodo-6′-methoxyphenoxy) methyl]-1-ethoxycarbonyl-1, 2, 5, 6,- tetrahydropyridine (11) reacted similarly to provide the tricyclic ANO fragment 12 in 70% ...