Stereocontrolled synthesis of polyenoic acids by a Heck-Sonogashira reaction:: easy access to 9,10-didehydro retinoic acids

被引:6
作者
Abarbri, M
Thibonnet, J
Parrain, JL
Duchêne, A
机构
[1] Fac Sci Tours, Lab Physicochim Interfaces & Milieux React, F-37200 Tours, France
[2] Fac Sci & Tech St Jerome, CNRS, UMR 6009, Synth Organ Lab, F-13397 Marseille 20, France
关键词
Heck-Sonogashira reactions; retinoids; alkenyl halides;
D O I
10.1016/S0040-4039(02)00807-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereo selective synthesis of rigid 9,10-didehydro retinoic acids was achieved from (2Z or 2E,4E)-5-iododienoic acids through a Heck-Sonogashira cross-coupling reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4703 / 4705
页数:3
相关论文
共 52 条
[1]  
Abarbri M, 1996, SYNTHESIS-STUTTGART, P82
[2]   AN EXPEDIENT ROUTE TO A VERSATILE INTERMEDIATE FOR THE STEREOSELECTIVE SYNTHESIS OF ALL-TRANS-RETINOIC ACID AND BETA-CAROTENE [J].
BABLER, JH ;
SCHLIDT, SA .
TETRAHEDRON LETTERS, 1992, 33 (50) :7697-7700
[3]   Regioselective synthesis of natural and unnatural (Z)-3-(1-alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2-hydroxybenzoates [J].
Bellina, F ;
Ciucci, D ;
Vergamini, P ;
Rossi, R .
TETRAHEDRON, 2000, 56 (16) :2533-2545
[4]   An efficient and stereoselective synthesis of 9-cis-retinoic acid [J].
Bennani, YL .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3542-3544
[5]   SYNTHESES OF HIGH SPECIFIC ACTIVITY 2,3-[H-3](2)-9-CIS-RETINOIC-ACID AND 3,4-[H-3](2)-9-CIS-RETINOIC-ACID [J].
BENNANI, YL ;
BOEHM, MF .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1195-1200
[6]   ELIMINATION OF ARYLSULFONYL GROUPS IN HETEROGENEOUS MEDIUM [J].
CHABARDES, P ;
DECOR, JP ;
VARAGNAT, J .
TETRAHEDRON, 1977, 33 (21) :2799-2805
[7]  
DAWSON MI, 1990, CHEM BIOL SYNTHETIC
[8]   Tetraenylstannanes in the synthesis of retinoic acid and its ring-modified analogues [J].
Domínguez, B ;
Iglesias, B ;
de Lera, AR .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :4135-4139
[9]   Stereocontrolled synthesis of 6-s-cis- and 6-s-trans-locked 9Z-retinoids by hydroxyl-accelerated Stille coupling of (Z)-tri-n-butylstannylbut-2-en-1-ol and bicyclic dienyl triflates [J].
Domínguez, B ;
Pazos, Y ;
de Lera, AR .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :5917-5925
[10]   A comprehensive survey of Stille-type Csp2-Csp2 single bond forming processes in the synthesis of retinoic acid and analogs [J].
Domínguez, B ;
Iglesias, B ;
de Lera, AR .
TETRAHEDRON, 1999, 55 (52) :15071-15098