Enantiospecific synthesis of cyanocyclitols and (6R)-6-hydroxyshikimic acid from benzonitrile

被引:21
作者
Carless, HAJ
Dove, Y
机构
[1] Department of Chemistry, Birkbeck College, Gordon House, London WC1H 0PP
关键词
D O I
10.1016/0957-4166(96)00055-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The chiral cis-3-cyanocyclohexa-3,5-diene-1,2-diol 5. available by microbial oxidation of benzonitrile, is the key intermediate used in brief syntheses of the cyanocyclitols 9 and 15, and in the synthesis of 6-hydroxyshikimic acid 20. (C) 1996 Elsevier Science Ltd
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收藏
页码:649 / 652
页数:4
相关论文
共 33 条
[21]  
LEY SV, 1992, SYNLETT, P997
[22]   AN APPROACH TO 6-OXYGENATED SHIKIMIC ACID-DERIVATIVES BY PHOTOLYSIS OF THE PYRUVATE ESTER OF DIMETHYL EPOXYCHORISMATE [J].
MEIER, RM ;
GANEM, B .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5436-5438
[23]   CATALYTIC PHOTOINDUCED CHARGE-TRANSFER OSMYLATION - A NOVEL PATHWAY FROM ARENES TO CYCLITOL DERIVATIVES [J].
MOTHERWELL, WB ;
WILLIAMS, AS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (18) :2031-2033
[24]   ENZYMATIC ACCESS TO HOMOCHIRAL L-ACETOXY-2-HYDROXYCYCLOHEXANE-3,5-DIENE THROUGH LIPASE-ASSISTED ACETYLATION IN ORGANIC-SOLVENT [J].
NICOLOSI, G ;
PATTI, A ;
PIATTELLI, M ;
SANFILIPPO, C .
TETRAHEDRON LETTERS, 1995, 36 (36) :6545-6546
[25]   DIELS-ALDER REACTIONS INVOLVING 1,2-ISOPROPYLIDENEDIOXY-3-TRIFLUOROMETHYLCYCLOHEXA-3,5-DIENE [J].
PITTOL, CA ;
PRYCE, RJ ;
ROBERTS, SM ;
RYBACK, G ;
SIK, V ;
WILLIAMS, JO .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (06) :1160-1162
[26]   CONVERSION OF BENZENE AND CHLOROBENZENE INTO POLYHYDROXYLATED CYCLOHEXANE DERIVATIVES RELATED TO CYCLOPHELLITOL [J].
ROBERTS, SM ;
SUTTON, PW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (12) :1499-1503
[27]  
Sheldrake G. N., 1992, CHIRALITY IND COMMER, P127
[28]  
SUAMI T, 1990, TOP CURR CHEM, V154, P257
[29]   CHEMISTRY OF CARBA-SUGARS (PSEUDO-SUGARS) AND THEIR DERIVATIVES [J].
SUAMI, T ;
OGAWA, S .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1990, 48 :21-90
[30]   THE SYNTHESIS OF 6-ALPHA-FLUOROSHIKIMIC AND 6-BETA-FLUOROSHIKIMIC ACIDS [J].
SUTHERLAND, JK ;
WATKINS, WJ ;
BAILEY, JP ;
CHAPMAN, AK ;
DAVIES, GM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) :1386-1387