STEREOCONTROLLED TOTAL SYNTHESIS OF LEUKOTRIENE-B4

被引:23
作者
AVIGNONTROPIS, M
BERJEAUD, JM
POUGNY, JR
FRECHARDORTUNO, I
GUILLERM, D
LINSTRUMELLE, G
机构
[1] ECOLE NORMALE SUPER,CNRS,CHIM LAB,24 RUE LHOMOND,F-75231 PARIS 05,FRANCE
[2] CNRS,CTR RECH BIOCHIM & GENET,F-31062 TOULOUSE,FRANCE
关键词
D O I
10.1021/jo00028a046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereocontrolled synthesis of leukotriene B4 (1) is accomplished by assembly of the chiral synthons 2 and 4, prepared from D-mannitol and 2-deoxy-D-ribose, with (E)-dichloroethylene.
引用
收藏
页码:651 / 654
页数:4
相关论文
共 24 条
[1]   AN EFFICIENT SYNTHESIS OF LEUKOTRIENE-B4 [J].
AVIGNONTROPIS, M ;
TREILHOU, M ;
LEBRETON, J ;
POUGNY, JR ;
FRECHARDORTUNO, I ;
HUYNH, C ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1989, 30 (46) :6335-6336
[2]   IMPROVED STEREOSELECTIVE REDUCTION OF A E,E, CONJUGATED DIENYNE TO A E,E,Z CONJUGATED TRIENE [J].
AVIGNONTROPIS, M ;
POUGNY, JR .
TETRAHEDRON LETTERS, 1989, 30 (37) :4951-4952
[3]   STEREOSPECIFIC SYNTHESES AND SPECTROSCOPIC PROPERTIES OF ISOMERIC 2,4,6,8-UNDECATETRAENES - NEW HYDROCARBONS FROM THE MARINE BROWN ALGA-GIFFORDIA-MITCHELLAE .4. [J].
BOLAND, W ;
SIELER, C ;
FEIGEL, M .
HELVETICA CHIMICA ACTA, 1987, 70 (04) :1025-1040
[4]   PROTON MAGNETIC-RESONANCE SPECTRA OF LEUKOTRIENE-A METHYL ESTER(I), LEUKOTRIENE-B METHYL-ESTER DIACETATE(II) AND 12-EPI-6-E,8-Z-LEUKOTRIENE-B METHYL-ESTER DIACETATE(III,5-S,12-S-DI-HETE) [J].
COREY, EJ ;
HOPKINS, PB ;
BARTON, AE ;
BANGERTER, B ;
BORGEAT, P .
TETRAHEDRON, 1982, 38 (17) :2653-2657
[5]   LEUKOTRIENE-B - TOTAL SYNTHESIS AND ASSIGNMENT OF STEREOCHEMISTRY [J].
COREY, EJ ;
MARFAT, A ;
GOTO, G ;
BRION, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) :7984-7985
[6]   A STEREOCONTROLLED AND EFFECTIVE SYNTHESIS OF LEUKOTRIENE-B-(1) [J].
COREY, EJ ;
MARFAT, A ;
MUNROE, J ;
KIM, KS ;
HOPKINS, PB ;
BRION, F .
TETRAHEDRON LETTERS, 1981, 22 (12) :1077-1080
[7]   LEUKOTRIENE-B, A POTENT CHEMOKINETIC AND AGGREGATING SUBSTANCE RELEASED FROM POLYMORPHONUCLEAR LEUKOCYTES [J].
FORDHUTCHINSON, AW ;
BRAY, MA ;
DOIG, MV ;
SHIPLEY, ME ;
SMITH, MJH .
NATURE, 1980, 286 (5770) :264-265
[8]   THE FACILE SYNTHESIS OF A LARGE RING LACTONE BY ACID-CATALYZED CYCLIZATION OF AN (Z)-ENE-DIYNE HYDROXY ACID PRECURSOR [J].
GUILLERM, D ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1985, 26 (32) :3811-3812
[9]   STEREOSELECTIVE SYNTHESIS OF POLYENIC ALCOHOLS - A NEW ROUTE TO THE LEUKOTRIENES-B [J].
GUILLERM, D ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1986, 27 (48) :5857-5860
[10]   STEREOSPECIFIC SYNTHESIS OF LEUKOTRIENE B4 (LTB4) [J].
GUINDON, Y ;
ZAMBONI, R ;
LAU, CK ;
ROKACH, J .
TETRAHEDRON LETTERS, 1982, 23 (07) :739-742