TOTAL STEREOSPECIFIC SYNTHESIS OF ALL CIS-5,8,11,14,17-EICOSAPENTAENOIC ACID (EPA)

被引:16
作者
VIALA, J
SANDRI, J
机构
[1] Laboratoire de Synthese Organique Associe au CNRS. Universite d'Aix-Marseille III -
关键词
ALL CIS-EICOSAPENTAENOIC ACID; EPA; CIS-WITTIG REACTION; OZONOLYSIS;
D O I
10.1016/S0040-4039(00)61227-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total stereospecific synthesis of EPA has been performed by a sequence of ozonolysis, selective reduction and Wittig reactions which affords the cis-skipped olefinic system. Versatile Compound 4, readily prepared from dihydro anisole, allowed us to prepare the skipped dienic synthon 2 in high yield.
引用
收藏
页码:4897 / 4900
页数:4
相关论文
共 22 条
[1]  
BELOSLUDTSEV YY, 1988, BIOORG KHIM+, V14, P100
[2]   P-2-NICKEL CATALYST WITH ETHYLENEDIAMINE, A NOVEL SYSTEM FOR HIGHLY STEREOSPECIFIC REDUCTION OF ALKYNES TO CIS-OLEFINS [J].
BROWN, CA ;
AHUJA, VK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (15) :553-554
[3]   SYNTHESIS OF OMEGA-TRITIATED AND OMEGA-FLUORINATED ANALOGS OF THE TRAIL PHEROMONE OF SUBTERRANEAN TERMITES [J].
CARVALHO, JF ;
PRESTWICH, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (07) :1251-1258
[4]   CONVENIENT METHOD FOR THE RECOVERY OF EICOSAPENTAENOIC ACID FROM COD LIVER OIL [J].
COREY, EJ ;
WRIGHT, SW .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (25) :5980-5981
[5]  
DAS UN, 1990, NUTRITION, V6, P429
[6]   TOTAL SYNTHESIS OF LEUKOTRIENE-E4 METABOLITES AND PRECURSORS TO RADIOLABELED FORMS OF THOSE METABOLITES [J].
DELORME, D ;
GIRARD, Y ;
ROKACH, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3635-3640
[7]  
DINARELLO CA, 1989, UCLA S MOL CELL BIOL, V100, P201
[8]  
DYERBERG J, 1986, NUTR REV, V44, P125, DOI 10.1111/j.1753-4887.1986.tb07603.x
[9]   EICOSAPENTANOIC ACID AND PREVENTION OF THROMBOSIS AND ATHEROSCLEROSIS [J].
DYERBERG, J ;
BANG, HO ;
STOFFERSEN, E ;
MONCADA, S ;
VANE, JR .
LANCET, 1978, 2 (8081) :117-119
[10]   ATHEROSCLEROSIS - CHRONIC EFFECTS OF FISH OIL AND A THERAPEUTIC DIET IN NONHUMAN-PRIMATES [J].
FINCHAM, JE ;
GOUWS, E ;
WOODROOF, CW ;
VANWYK, MJ ;
KRUGER, M ;
SMUTS, CM ;
VANJAARSVELD, PJ ;
TALJAARD, JJF ;
SCHALL, R ;
STRAUSS, JAD ;
BENADE, AJS .
ARTERIOSCLEROSIS AND THROMBOSIS, 1991, 11 (03) :719-732