TY - JOUR
T1 - Novel radical synthesis of morphine fragments spiro[benzofuran-3(2H),4'-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline
AU - Cheng, Chen Yu
AU - Hsin, Ling Wei
AU - Liou, Jing Ping
PY - 1996/8/12
Y1 - 1996/8/12
N2 - 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'-methoxyphenoxyl)methyl]-1-methyl-1,2,5,6-tetrahydropyr idine (9); while the tetrayclic (ACNO) fragmet 9-methoxy-3-methyl-2,3,4,4aα,5,6,7,7aα-octahydro-1H-benzofuro[3,2-e] isoquinoline (3) and its 4-oxo analog 4 were synthesized in a similar fashion starting from 5,6,7,8-tetrahydroisoquinoline (10).
AB - 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'-methoxyphenoxyl)methyl]-1-methyl-1,2,5,6-tetrahydropyr idine (9); while the tetrayclic (ACNO) fragmet 9-methoxy-3-methyl-2,3,4,4aα,5,6,7,7aα-octahydro-1H-benzofuro[3,2-e] isoquinoline (3) and its 4-oxo analog 4 were synthesized in a similar fashion starting from 5,6,7,8-tetrahydroisoquinoline (10).
UR - http://www.scopus.com/inward/record.url?scp=0030581405&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030581405&partnerID=8YFLogxK
U2 - 10.1016/0040-4020(96)00649-7
DO - 10.1016/0040-4020(96)00649-7
M3 - Article
AN - SCOPUS:0030581405
SN - 0040-4020
VL - 52
SP - 10935
EP - 10944
JO - Tetrahedron
JF - Tetrahedron
IS - 33
ER -