HIGHLY STEREOCONTROLLED PROTON-TRANSFER IN AN ENAMMONIUM IMINIUM REARRANGEMENT - MECHANISM OF THE STEREOSELECTIVE DEOXYGENATION OF 6-ARYL-6-HYDROXY-1,2,3,5,6,10B-HEXAHYDROPYRROLO[2,1-A]ISOQUINOLINES WITH BORANE-THF IN TRIFLUOROACETIC-ACID

被引:14
作者
MARYANOFF, BE [1 ]
MCCOMSEY, DF [1 ]
MUTTER, MS [1 ]
SORGI, KL [1 ]
MARYANOFF, CA [1 ]
机构
[1] MCNEIL PHARMACEUT,DEPT CHEM DEV,SPRING HOUSE,PA 19477
关键词
D O I
10.1016/S0040-4039(00)80682-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:5073 / 5076
页数:4
相关论文
共 16 条
[1]  
Blaha K., 1966, ADV HETEROCYCL CH, V6, P147, DOI [10.1016/S0065-2725(08)60577-2, DOI 10.1016/S0065-2725(08)60577-2]
[2]  
Cook A. G., 1988, ENAMINES SYNTHESIS S
[3]   SYNTHESIS OF 9,10,12,13,14,14A-HEXAHYDRODIBENZO[F,H]PYRROLO-[2,1-A]ISOQUINOLINE [J].
COPADO, R ;
GRANDE, MT ;
TRIGO, GG ;
SOLLHUBER, MM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (02) :601-603
[4]  
Dyke S. F., 1972, ADVANCES HETEROCYCLI, V14, P279
[5]   APPLICATION OF METALATED ENAMINES TO ALKALOID SYNTHESIS - AN EXPEDIENT APPROACH TO THE SYNTHESIS OF MORPHINE-BASED ANALGESICS [J].
EVANS, DA ;
MITCH, CH ;
THOMAS, RC ;
ZIMMERMAN, DM ;
ROBEY, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5955-5956
[6]   SODIUM-BOROHYDRIDE IN CARBOXYLIC-ACID MEDIA - A REVIEW OF THE SYNTHETIC UTILITY OF ACYLOXYBOROHYDRIDES [J].
GRIBBLE, GW ;
NUTAITIS, CF .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1985, 17 (4-5) :317-384
[7]  
KURSANOV DN, 1974, SYNTHESIS-STUTTGART, P633
[8]  
MARYANOFF B E, 1986, Drugs of the Future, V11, P18
[9]   BORANE COMPLEXES IN TRIFLUOROACETIC-ACID - REDUCTION OF INDOLES TO INDOLINES AND GENERATION OF BIS(TRIFLUOROACETOXY)BORANE [J].
MARYANOFF, BE ;
MCCOMSEY, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (13) :2733-2734
[10]   PROPERTIES OF BIS(TRIFLUOROACETOXY)BORANE AS A REDUCING AGENT OF ORGANIC-COMPOUNDS [J].
MARYANOFF, BE ;
MCCOMSEY, DF ;
NORTEY, SO .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) :355-360