PREPARATION OF OPIUM-ALKALOIDS BY PALLADIUM-CATALYZED BIS-CYCLIZATIONS - FORMAL TOTAL SYNTHESIS OF MORPHINE

被引:36
作者
HONG, CY [1 ]
OVERMAN, LE [1 ]
机构
[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
关键词
D O I
10.1016/S0040-4039(00)73208-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium catalyzed cyclization of hydroisoquinoline diene 10 to afford the pentacyclic opiate 11 is the central step in a new synthesis of opium alkaloids.
引用
收藏
页码:3453 / 3456
页数:4
相关论文
共 10 条
[1]   SIMPLE METHOD FOR CONTROLLING STEREOSELECTION IN MANNICH CYCLIZATION REACTIONS OF ALDEHYDES [J].
HEERDING, DA ;
HONG, CY ;
KADO, N ;
LOOK, GC ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6947-6948
[2]   ASYMMETRIC-SYNTHESIS OF EITHER ENANTIOMER OF OPIUM-ALKALOIDS AND MORPHINANS - TOTAL SYNTHESIS OF (-)-DIHYDROCODEINONE AND (+)-DIHYDROCODEINONE AND (-)-MORPHINE AND (+)-MORPHINE [J].
HONG, CY ;
KADO, N ;
OVERMAN, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11028-11029
[3]  
IIJIMA I, 1977, HETEROCYCLES, V6, P1157
[4]   PALLADIUM-CATALYZED HETEROANNULATION OF 1,3-DIENES BY FUNCTIONALLY SUBSTITUTED ARYL HALIDES [J].
LAROCK, RC ;
BERRIOSPENA, N ;
NARAYANAN, K .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3447-3450
[5]   PALLADIUM-CATALYZED REACTIONS OF KETONE ALPHA-CARBONATES WITH NORBORNENES - AN UNUSUAL CYCLOPROPANATION [J].
OGOSHI, S ;
MORIMOTO, T ;
NISHIO, K ;
OHE, K ;
MURAI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :9-10
[6]  
OVERMAN LE, 1994, IN PRESS PURE APPL C
[7]   OSMIUM TETROXIDE-CATALYZED PERIODATE OXIDATION OF OLEFINIC BONDS [J].
PAPPO, R ;
ALLEN, DS ;
LEMIEUX, RU ;
JOHNSON, WS .
JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :478-479
[8]   CONVERGENT SYNTHESIS OF (+/-)-DIHYDROISOCODEINE IN 11 STEPS BY THE TANDEM RADICAL CYCLIZATION STRATEGY - A FORMAL TOTAL SYNTHESIS OF (+/-)-MORPHINE [J].
PARKER, KA ;
FOKAS, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9688-9689
[9]   ALLYLIC OXIDATION WITH 3,5-DIMETHYLPYRAZOLE - CHROMIUM TRIOXIDE COMPLEX - STEROIDAL DELTA-5-7-KETONES [J].
SALMOND, WG ;
BARTA, MA ;
HAVENS, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :2057-2059
[10]   A NOVEL-APPROACH TO THE SYNTHESIS OF MORPHINE ALKALOIDS - THE SYNTHESIS OF (D,L)-THEBAINONE-A [J].
TIUS, MA ;
KERR, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :5959-5966