Construction of (Z,Z) skipped 1,4-dienes.: Application to the synthesis of polyunsaturated fatty acids and derivatives

被引:69
作者
Durand, S [1 ]
Parrain, JL [1 ]
Santelli, M [1 ]
机构
[1] Fac Sci St Jerome, CNRS, Synth Organ Lab, F-13397 Marseille, France
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 03期
关键词
D O I
10.1039/a907643c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The construction of (Z,Z) skipped 1,4-dienes was presented. Methods to prepare skipped diene moiety and their application to the synthesis of polyunsaturated fatty acids (PUFA) and derivatives was discussed. PUFA has also emerged as carriers of the skipped diene moiety both for PUFA metabolites synthesis and for biosynthetic studies.
引用
收藏
页码:253 / 273
页数:21
相关论文
共 131 条
[1]   Synthesis of putative Delta(6)-, Delta(12)- and Delta(15)-desaturase inhibitors [J].
AlDulayymi, JR ;
Baird, MS ;
Dale, CM ;
Grehan, BJ ;
Shortt, MF .
TETRAHEDRON, 1997, 53 (03) :1099-1110
[2]   A FACILE PREPARATION OF 2(Z), 5(Z), 8(Z)-TETRADECATRIEN-1-OL - A KEY INTERMEDIATE FOR EICOSANOID SYNTHESIS [J].
BADONE, D ;
PAGLIARIN, R ;
SISTI, M ;
TAVECCHIA, P .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1989, 21 (05) :629-632
[3]   THE INVENTION OF RADICAL REACTIONS .18. A CONVENIENT SOLUTION TO THE 1-CARBON PROBLEM (R-CO2H-](R-CO2H)-C-13) [J].
BARTON, DHR ;
OZBALIK, N ;
VACHER, B .
TETRAHEDRON, 1988, 44 (12) :3501-3512
[4]   IDENTIFICATION AND ENANTIOSELECTIVE SYNTHESIS OF (Z,Z)-6,9-CIS-3S,4R-EPOXYNONADECADIENE, THE MAJOR SEX-PHEROMONE COMPONENT OF BOARMIA-SELENARIA [J].
BECKER, D ;
CYJON, R ;
COSSE, A ;
MOORE, I ;
KIMMEL, T ;
WYSOKI, M .
TETRAHEDRON LETTERS, 1990, 31 (34) :4923-4926
[5]   A NEW PRACTICAL METHOD FOR THE PREPARATION OF [H-3(6)]-LEUKOTRIENES C-4 AND D-4 [J].
BELLEY, ML ;
GAREAU, Y ;
ZAMBONI, RJ ;
AHERN, DG ;
HONG, Y .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1995, 36 (06) :599-609
[6]   SYNTHESIS OF (9Z,12E)-[1-C-148LINOLEIC AND (9E,12Z)-[1-C-14]LINOLEIC ACID AND (5Z,8Z,11Z,14E)-[1-C-14]ARACHIDONIC ACID [J].
BERDEAUX, O ;
VATELE, JM ;
EYNARD, T ;
NOUR, M ;
POULLAIN, D ;
NOEL, JP ;
SEBEDIO, JL .
CHEMISTRY AND PHYSICS OF LIPIDS, 1995, 78 (01) :71-80
[7]  
BODEN CDJ, 1993, SYNTHESIS-STUTTGART, P411, DOI 10.1055/s-1993-25874
[8]  
BROEKHOF NLJM, 1986, RECL TRAV CHIM PAY B, V105, P436
[9]   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
[10]   CATALYTIC-HYDROGENATION .6. REACTION OF SODIUM-BOROHYDRIDE WITH NICKEL SALTS IN ETHANOL SOLUTION - P-2 NICKEL, A HIGHLY CONVENIENT, NEW, SELECTIVE HYDROGENATION CATALYST WITH GREAT SENSITIVITY TO SUBSTRATE STRUCTURE [J].
BROWN, CA ;
AHUJA, VK .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (12) :2226-2230