AN EFFICIENT SYNTHESIS OF A CHIRAL CARBOCYCLIC 2'-DEOXYRIBONUCLEOSIDE SYNTHON BY DIRECTED REDUCTION

被引:16
作者
BORTHWICK, AD
CRAME, AJ
EXALL, AM
WEINGARTEN, GG
机构
[1] Department of Medicinal Chemistry II, Glaxo Research and Development Ltd, Greenford
关键词
D O I
10.1016/S0040-4039(00)78373-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Directed reduction of the 1,4 hydroxy-ketone 9 and the 1,4 aldehydo-ketone 12 with NaBH(OAc)(3) gave stereoselectively in high yield the 1,4 diol 10, a key intermediate required in our synthesis of chiral carbocyclic 2'-deoxyribonucleosides.
引用
收藏
页码:7677 / 7680
页数:4
相关论文
共 28 条
[1]   DIASTEREOSELECTIVITY IN THE SYNTHESIS OF 3(2H)-FURANONES - TOTAL SYNTHESIS OF (+)-MUSCARINE [J].
ADAMS, J ;
POUPART, MA ;
GRENIER, L .
TETRAHEDRON LETTERS, 1989, 30 (14) :1753-1756
[3]   SHORT CONVERGENT ROUTE TO HOMOCHIRAL CARBOCYCLIC 2'-DEOXYNUCLEOSIDES AND CARBOCYCLIC RIBONUCLEOSIDES [J].
BIGGADIKE, K ;
BORTHWICK, AD ;
EXALL, AM ;
KIRK, BE ;
ROBERTS, SM ;
YOUDS, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (14) :1083-1084
[4]   SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].
BORTHWICK, AD ;
BIGGADIKE, K .
TETRAHEDRON, 1992, 48 (04) :571-623
[5]   SYNTHESIS OF (ALKOXYMETHYL)ZIRCONOCENE CHLORIDES - STEREOCHEMISTRY OF CARBON CARBON BOND FORMATION IN A ZIRCONOCENE-WITTIG REARRANGEMENT [J].
BUCHWALD, SL ;
NIELSEN, RB ;
DEWAN, JC .
ORGANOMETALLICS, 1989, 8 (07) :1593-1598
[6]   A NOVEL AND EFFICIENT ROUTE TO CHIRAL 2-SUBSTITUTED CARBOCYCLIC 5'-N-ETHYL-CARBOXAMIDO-ADENOSINE (C-NECA) [J].
CHEN, J ;
GRIM, M ;
ROCK, C ;
CHAN, K .
TETRAHEDRON LETTERS, 1989, 30 (41) :5543-5546
[7]   NOVEL STEREOSPECIFIC SILYL GROUP TRANSFER-REACTIONS - PRACTICAL ROUTES TO THE PROSTAGLANDINS [J].
DANISHEFSKY, SJ ;
CABAL, MP ;
CHOW, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3456-3457
[8]   DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].
EVANS, DA ;
CHAPMAN, KT ;
CARREIRA, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578
[9]   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
[10]   SYNTHETIC STUDIES ON THE MEVINIC ACIDS USING THE CHIRON APPROACH - TOTAL SYNTHESIS OF (+)-DIHYDROMEVINOLIN [J].
HANESSIAN, S ;
ROY, PJ ;
PETRINI, M ;
HODGES, PJ ;
DIFABIO, R ;
CARGANICO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5766-5777