ANTHRACYCLINES .13. THE SYNTHESIS OF (+)-(4R,6R) AND (+)-(4S,6R)-6-ACETYL-6-(TERT-BUTYLDIMETHYLSILYLOXY)-4-ETHOXY-4-METHOXY-5,6,7,8-TETRAHYDRONAPHTHALEN-1(4H)-ONE - NEW CHIRAL AB SYNTHONS FOR THE SYNTHESIS OF (-)-7-DEOXYDAUNOMYCINONE

被引:7
作者
RUSSELL, RA [1 ]
IRVINE, RW [1 ]
WARRENER, RN [1 ]
机构
[1] AUSTRALIAN NATL UNIV FAC,DEPT CHEM,CANBERRA,ACT 2601,AUSTRALIA
关键词
D O I
10.1071/CH9850189
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:189 / 195
页数:7
相关论文
共 10 条
[1]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[2]   A NOVEL METHOXY-DIRECTED KETAL HYDROLYSIS AND ITS APPLICATION TO A CONVERGENT, REGIOSPECIFIC SYNTHESIS OF (+/-)-DAUNOMYCINONE [J].
DOLSON, MG ;
CHENARD, BL ;
SWENTON, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (17) :5263-5264
[3]  
Ireland R. E., 1977, ORG SYNTH, V56, P44
[4]   MECHANISTIC STUDIES REGARDING OXIDATION OF ALCOHOLS BY SILVER CARBONATE ON CELITE [J].
KAKIS, FJ ;
FETIZON, M ;
DOUCHKINE, N ;
GOLFIER, M ;
MOURGUES, P ;
PRANGE, T .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (04) :523-533
[5]   AN EXCEPTIONAL 5-ENDO-TRIG REVERSAL - A CONVERGENT SYNTHESIS OF DAUNOMYCINONE [J].
KEAY, BA ;
RODRIGO, R .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (03) :637-639
[6]   FACILE REGIOSELECTIVE AND STEREOSELECTIVE TOTAL SYNTHESIS OF RACEMIC AKLAVINONE [J].
LI, TT ;
WU, YL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (23) :7007-7009
[7]   THE REGIOSPECIFIC PREPARATION OF 1,4-DIOXYGENATED ANTHRAQUINONES - A NEW ROUTE TO ISLANDICIN, DIGITOPURPONE, AND MADEIRIN [J].
RUSSELL, RA ;
WARRENER, RN .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (03) :108-110
[8]   ANTHRACYCLINES .12. THE PREPARATION OF (-)-(7R)-7-ACETYL-7-(TERT-BUTYLDIMETHYLSILYLOXY)-4,4-DIMETHOXY-5,6,7,8-TETRAHYDRONAPHTHALENE-1(4H)-ONE AND (+)-(6R)-6-ACETYL-6-(TERT-BUTYLDIMETHYLSILYLOXY)-4,4-DIMETHOXY-5,6,7,8-TETRAHYDRONAPHTHALENE-1(4H)-ONE - AN IMPROVED ROUTE TO CHIRAL AB SYNTHONS FOR 7-DEOXYDAUNOMYCINONED [J].
RUSSELL, RA ;
KRAUSS, AS ;
IRVINE, RW ;
WARRENER, RN .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (01) :179-187
[9]   ANTHRACYCLINES .10. THE ENANTIOSPECIFIC SYNTHESIS OF (-)-(7R)-7-ACETYL-7-HYDROXY-4,4-DIMETHOXY-5,6,7,8-TETRAHYDRONAPHTHALEN-1(4H)-ONE - A TYPE-I CHIRAL DIENONE FOR THE SYNTHESIS OF 7-DEOXYDAUNOMYCINONE [J].
RUSSELL, RA ;
GEE, PS ;
IRVINE, RW ;
WARRENER, RN .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (08) :1709-1720
[10]   A NOVEL RACEMIZATION MECHANISM FOR THE ALPHA-HYDROXY KETONE MOIETY (C9-POSITION) OF OPTICALLY-ACTIVE ANTHRACYCLINONE DERIVATIVES [J].
TERASHIMA, S ;
TAMOTO, K .
TETRAHEDRON LETTERS, 1983, 24 (25) :2589-2592