TY - JOUR
T1 - Synthesis of morphine fragments spiro[benzofuran-3(2H),4'-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline by intramolecular heck reaction
AU - Cheng, Chen Yu
AU - Liou, Jing Ping
AU - Lee, Mei Jing
PY - 1997/6/30
Y1 - 1997/6/30
N2 - 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% yield and 45% e.e. when a Pd-(S)-BINAP complex was used as the catalyst.
AB - 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% yield and 45% e.e. when a Pd-(S)-BINAP complex was used as the catalyst.
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U2 - 10.1016/S0040-4039(97)00976-3
DO - 10.1016/S0040-4039(97)00976-3
M3 - Article
AN - SCOPUS:0031004433
SN - 0040-4039
VL - 38
SP - 4571
EP - 4574
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 26
ER -