Stereoselective synthesis of conjugated α-Z/γ-E and α-Z/γ-Z dienoic acids. Kinetic torquoselectivity versus thermodynamic control

被引:12
作者
Agarwal, Jyoti [1 ]
Bayounes, Ouahiba [1 ]
Thorimbert, Serge [1 ]
Dechoux, Luc [1 ]
机构
[1] Univ Paris 06, Inst Parisien Chim Mol, UMR CNRS 7201, F-75005 Paris, France
来源
RSC ADVANCES | 2014年 / 4卷 / 06期
关键词
DERIVATIVES; 2-PYRONES; PYRANE; DFT;
D O I
10.1039/c3ra45309j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stereoselective synthesis of conjugated (alpha-Z/gamma-E)-(alpha-Z/gamma-Z)-dienoic acids 4 and 4' is described. It is based on the regio- and stereoselective addition of Grignard reagents to methylcoumalate. The origin of the stereocontrol is discussed.
引用
收藏
页码:2772 / 2775
页数:4
相关论文
共 45 条
[1]  
Abarbri M, 1996, SYNTHESIS-STUTTGART, P82
[2]   Stereoselective synthesis of trienoic acids: Synthesis of retinoic acids and analogues [J].
Abarbri, Mohamed ;
Parrain, Jean-Luc ;
Duchene, Alain ;
Thibonnet, Jerome .
SYNTHESIS-STUTTGART, 2006, (17) :2951-2970
[3]   DFT study of pericyclic reaction cascades in the synthesis of antibiotic TAN-1085 [J].
Akerling, ZR ;
Norton, JE ;
Houk, KN .
ORGANIC LETTERS, 2004, 6 (23) :4273-4275
[4]   Chemoselective 1,3-dipolar cycloadditions of azomethine ylide with conjugated dienes [J].
Blumberg, Laura C. ;
Costa, Brian ;
Goldstein, Rebecca .
TETRAHEDRON LETTERS, 2011, 52 (08) :872-874
[5]   A general synthesis of (2Z)-terpenoic acids [J].
Cahard, D ;
Mammeri, M ;
Poirier, JM ;
Duhamel, L .
TETRAHEDRON LETTERS, 2000, 41 (19) :3619-3622
[6]   Substituted 2-sulfonamido-5-aminopyridines II [J].
Caldwell, WT ;
Tyson, FT ;
Lauer, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1479-1484
[7]   SYNTHESIS OF COMPOUNDS CONTAINING ISOPRENE UNIT - STEREOSPECIFIC SYNTHESIS OF DEHYDRONEROL ISOVALERATE - COMPONENT OF ANTHEMIS-MONTANA L [J].
CARDILLO, G ;
ORENA, M ;
SANDRI, S .
TETRAHEDRON, 1976, 32 (01) :107-108
[8]   Synthesis and preliminary biological characterization of new semisynthetic derivatives of ramoplanin [J].
Ciabatti, Romeo ;
Maffioli, Sonia I. ;
Panzone, Gianbattista ;
Canavesi, Augusto ;
Michelucci, Elena ;
Tiseni, Paolo S. ;
Marzorati, Ettore ;
Checchia, Anna ;
Giannone, Matteo ;
Jabes, Daniela ;
Romano, Gabriella ;
Brunati, Cristina ;
Candiani, Gianpaolo ;
Castiglione, Franca .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (13) :3077-3085
[9]   A NOVEL SYNTHESIS OF (+/-)-ABSCISIC ACID [J].
CONSTANTINO, MG ;
LOSCO, P ;
CASTELLANO, EE .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :681-683
[10]  
COREY EJ, 1979, TETRAHEDRON LETT, P2317