VIC-DIOL CHIRONS - ENANTIOSPECIFIC SYNTHESIS OF 11,12-DIHYDROXYEICOSATRIENOIC AND 14,15-DIHYDROXYEICOSATRIENOIC ACIDS

被引:3
作者
CHAUHAN, K
ARAVIND, S
LEE, SG
FALCK, JR
CAPDEVILA, JH
机构
[1] UNIV TEXAS,SW MED CTR,DEPT MOLEC GENET,DALLAS,TX 75235
[2] UNIV TEXAS,SW MED CTR,DEPT PHARMACOL,DALLAS,TX 75235
[3] VANDERBILT UNIV,SCH MED,DEPT MED,NASHVILLE,TN 37205
[4] VANDERBILT UNIV,SCH MED,DEPT BIOCHEM,NASHVILLE,TN 37205
关键词
D O I
10.1016/0040-4039(94)85006-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A differentiated, six-carbon vicinal-diol chiron was prepared from D-glucurono-6,3-lactone and exploited in the asymmetric synthesis of the erythro/threo-isomers of the title eicosanoids.
引用
收藏
页码:6791 / 6794
页数:4
相关论文
共 17 条
[1]   ENANTIOMERIC SYNTHESES OF 6(R), 7(R) AND 6(S), 7(S) TRANS-LAUREDIOL AND CIS-LAUREDIOL [J].
ANORBE, B ;
MARTIN, VS ;
PALAZON, JM ;
TRUJILLO, JM .
TETRAHEDRON LETTERS, 1986, 27 (41) :4991-4994
[2]   EPOXY LIPIDS FROM THE AUSTRALIAN EPIPHYTIC BROWN ALGA NOTHEIA-ANOMALA [J].
BARROW, RA ;
CAPON, RJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (05) :895-911
[3]   RESOLUTION OF DIHYDROXYEICOSANOATES AND OF DIHYDROXYEICOSATRIENOATES BY CHIRAL PHASE CHROMATOGRAPHY [J].
CAPDEVILA, JH ;
WEI, SZ ;
KUMAR, A ;
KOBAYASHI, J ;
SNAPPER, JR ;
ZELDIN, DC ;
BHATT, RK ;
FALCK, JR .
ANALYTICAL BIOCHEMISTRY, 1992, 207 (02) :236-240
[4]  
CAPDEVILA JH, 1992, J BIOL CHEM, V267, P21720
[5]   CYTOCHROME-P450 AND THE ARACHIDONATE CASCADE [J].
CAPDEVILA, JH ;
FALCK, JR ;
ESTABROOK, RW .
FASEB JOURNAL, 1992, 6 (02) :731-736
[6]   ENDOGENOUS BIOSYNTHESIS OF ARACHIDONIC-ACID EPOXIDES IN HUMANS - INCREASED FORMATION IN PREGNANCY-INDUCED HYPERTENSION [J].
CATELLA, F ;
LAWSON, JA ;
FITZGERALD, DJ ;
FITZGERALD, GA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (15) :5893-5897
[7]  
Dax K., 1976, ADV CARBOHYD CHEM BI, V33, P189, DOI DOI 10.1016/S0065-2318(08)60282-6
[8]   CYTOCHROME P450 METABOLITES OF ARACHIDONIC-ACID ARE POTENT INHIBITORS OF VASOPRESSIN ACTION ON RABBIT CORTICAL COLLECTING DUCT [J].
HIRT, DL ;
CAPDEVILA, J ;
FALCK, JR ;
BREYER, MD ;
JACOBSON, HR .
JOURNAL OF CLINICAL INVESTIGATION, 1989, 84 (06) :1805-1812
[9]  
Hughes D.L., 1992, ORGANIC REACTIONS, P335
[10]  
LIN GQ, 1985, TETRAHEDRON LETT, V26, P1233