Tetrahedron

Novel radical synthesis of morphine fragments spiro [benzofuran-3 (2H), 4′-piperidine] and octahydro-1H-benzofuro [3, 2-e] isoquinoline

CY Cheng, LW Hsin, JP Liou

Index: Cheng, Chen-Yu; Hsin, Ling-Wei; Liou, Jing-Ping Tetrahedron, 1996 , vol. 52, # 33 p. 10935 - 10944

Full Text: HTML

Citation Number: 23

Abstract

A new strategy for the synthesis of oxide-containing fragments of morphine has been developed. Thus, the tricyclic (ANO) morphine fragment spiro [7-methoxybenzofuran-3 (2H), 4′-1′-methylpiperidine](1) was obtained as the sole product via an intramolecular radical cyclization of 4-[(2′-bromo-6′-methoxyphenoxy) methyl]-1-methyl-1, 2, 5, 6,- tetrahydropyridine (9); while the tetracyclic (ACNO) fragment 9-methoxy-3-methyl-2, 3, 4, ...