THE RADICAL CYCLIZATION APPROACH TO MORPHINE - MODELS FOR HIGHLY OXYGENATED RING-III SYNTHONS

被引:42
作者
PARKER, KA
FOKAS, D
机构
[1] Department of Chemistry, Brown University, Providence
关键词
D O I
10.1021/jo00093a027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Iodo-3-methyl-2-cyclohexenone (9) and 3-alkyl 3-cyclohexene-1,2-diol derivatives 16 were examined as ring-III equivalents for the tandem radical cyclization approach to the synthesis of morphine (1a).
引用
收藏
页码:3933 / 3938
页数:6
相关论文
共 12 条
[1]  
BROTHERTON RJ, 1962, ORG CHEM, V27, P3253
[2]   LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].
GEMAL, AL ;
LUCHE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459
[3]  
JACOBS J, 1979, J ORG CHEM, V44, P449
[4]   NEW ROUTE TO CYCLOPENTENE-1-CARBOXALDEHYDES BY REARRANGEMENT OF 2,3-EPOXYCYCLOHEXANOLS [J].
MAGNUSSO.G ;
THOREN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (07) :1380-1384
[5]   INTRAMOLECULAR ADDITIONS OF ALLYLSILANES TO CONJUGATED DIENONES - THE SYNTHESIS OF 3 PERFORANES [J].
MAJETICH, G ;
DEFAUW, J ;
RINGOLD, C .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :50-68
[6]   REARRANGEMENT REACTIONS OF 4-BROMOISOPHORONE [J].
MARX, JN ;
CARNRICK, AW ;
COX, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (14) :2308-&
[7]   EPOXY ALCOHOL REARRANGEMENTS - HYDROXYL-MEDIATED DELIVERY OF LEWIS ACID PROMOTERS [J].
MORGANS, DJ ;
SHARPLESS, KB ;
TRAYNOR, SG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (02) :462-464
[8]   RADICAL CYCLIZATIONS IN CONFORMATIONALLY RESTRAINED SYSTEMS - GENERATION OF THE CIS,CIS-HEXAHYDROPHENANTHRO(4,5-BCD)FURAN TETRACYCLE OF MORPHINE [J].
PARKER, KA ;
SPERO, DM ;
VANEPP, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4628-4630
[9]   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
[10]   STEREOCHEMISTRY OF RADICAL CYCLIZATIONS TO SIDE-CHAIN OLEFINIC BONDS - AN APPROACH TO CONTROL OF THE C-9 CENTER OF MORPHINE [J].
PARKER, KA ;
FOKAS, D .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :3927-3932