A key intermediate towards oxylipins.: A formal synthesis of (12S)-HETE and (12S)-LTB4

被引:6
作者
Benkouider, A
Pale, P
机构
[1] Univ Strasbourg 1, Lab Synth & React Organ, F-67000 Strasbourg, France
[2] Univ Reims, CNRS, Chim Organ Phys Lab, F-51100 Reims, France
来源
JOURNAL OF CHEMICAL RESEARCH-S | 1999年 / 02期
关键词
D O I
10.1039/a807074a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A key intermediate in the synthesis of various oxylipins, the optically active (3S,5Z)-3-methoxymethoxyundec-5-en-1-yne, has been obtained in 11 steps starting from propane-1,3-diol, with an overall yield of 14%.
引用
收藏
页码:104 / 105
页数:3
相关论文
共 24 条
[1]  
BENKOUIDER A, 1994, THESIS U REIMS CHAMP
[2]   EICOSANOIDS FROM THE TROPICAL RED-ALGA MURRAYELLA-PERICLADOS [J].
BERNART, MW ;
GERWICK, WH .
PHYTOCHEMISTRY, 1994, 36 (05) :1233-1240
[3]   ASYMMETRIC REDUCTION WITH CHIRAL ORGANOBORANES BASED ON ALPHA-PINENE [J].
BROWN, HC ;
RAMACHANDRAN, PV .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (01) :16-24
[4]   A SHORT STEREOCONTROLLED SYNTHESIS OF LEUKOTRIENE-B4 [J].
CHEMIN, D ;
LINSTRUMELLE, G .
TETRAHEDRON, 1992, 48 (10) :1943-1952
[5]   NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES [J].
COREY, EJ ;
HELAL, CJ .
TETRAHEDRON LETTERS, 1995, 36 (50) :9153-9156
[6]  
Gerwick W.H., 1993, MARINE BIOTECHNOLOGY, P101
[7]   CARBOCYCLIC OXYLIPINS OF MARINE ORIGIN [J].
GERWICK, WH .
CHEMICAL REVIEWS, 1993, 93 (05) :1807-1823
[8]   ENZYMATIC-HYDROLYSIS OF CYCLOPROPANES - TOTAL SYNTHESIS OF OPTICALLY PURE DICTYOPTERENE-A AND DICTYOPTERENE-C' [J].
GRANDJEAN, D ;
PALE, P ;
CHUCHE, J .
TETRAHEDRON, 1991, 47 (07) :1215-1230
[9]   Direct catalytic enantioselective reduction of achiral alpha,beta-ynones. Strong remote steric effects across the C-C triple bond [J].
Helal, CJ ;
Magriotis, PA ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) :10938-10939
[10]  
MIDLAND MM, 1984, TETRAHEDRON, V40, P1371