Catalytic Activity Studies of Aminocarbonyl Group Containing Hoveyda-Grubbs-Type Complexes for the Syntheses of Herbarumin I and Stagonolide A

被引:27
作者
Mohapatra, Debendra K. [1 ]
Somaiah, R. [1 ]
Rao, M. Mallikarjuna [1 ]
Caijo, Frederic [2 ]
Mauduit, Marc [2 ]
Yadav, J. S. [1 ]
机构
[1] Indian Inst Chem Technol CSIR, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
[2] Ecole Natl Super Chim Rennes, F-35700 Rennes, France
关键词
decanolides; stagonolides; herbarumin I; Wittig reaction; ring-closing metathesis; RING-CLOSING METATHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; OLEFIN METATHESIS; PHYTOTOXIC NONENOLIDE; STAGONOSPORA-CIRSII; PHOMA-PUTAMINUM; STEREOSELECTIVE-SYNTHESIS; POTENTIAL MYCOHERBICIDE; ASCOCHYTA-PINODES; ORGANIC-SYNTHESIS;
D O I
10.1055/s-0029-1219807
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic activity of four aminocarbonyl group containing 'boomerang'-type ring-closing metathesis catalysts have been studied for ten-membered lactone and compared well with the Grubbs I and II as well as the Hoveyda-Grubbs catalysts. The activity was found to be superior to the above three ring-closing metathesis catalysts and suggesting novel stereoselective total syntheses of herbarumin I and stagonolide A.
引用
收藏
页码:1223 / 1226
页数:4
相关论文
共 50 条
[1]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[2]   A short enantioselective total synthesis of the phytotoxic lactone herbarumin III [J].
Boruwa, Joshodeep ;
Gogoi, Naminita ;
Barua, Nabin C. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (18) :3521-3525
[3]   Towards Long-Living Metathesis Catalysts by Tuning the N-Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide-Activated Boomerang Ru Complexes [J].
Clavier, Herve ;
Caijo, Frederic ;
Borre, Etienne ;
Rix, Diane ;
Boeda, Fabien ;
Nolan, Steven P. ;
Mauduit, Marc .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (25) :4254-4265
[4]  
COREY EJ, 1976, TETRAHEDRON LETT, V17, P809
[5]   Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].
Deiters, A ;
Martin, SF .
CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238
[6]   The use of butane diacetals of glycolic acid as precursors for the synthesis of the phytotoxic calmodulin inhibitor herbarumin II [J].
Díez, E ;
Dixon, DJ ;
Ley, SV ;
Polara, A ;
Rodríguez, F .
HELVETICA CHIMICA ACTA, 2003, 86 (11) :3717-3729
[7]   Decanolides, 10-membered lactones of natural origin [J].
Drager, G ;
Kirschning, A ;
Thiericke, R ;
Zerlin, M .
NATURAL PRODUCT REPORTS, 1996, 13 (05) :365-375
[8]   Putaminoxins D and E from Phoma putaminum [J].
Evidente, A ;
Capasso, R ;
Andolfi, A ;
Vurro, M ;
Zonno, MC .
PHYTOCHEMISTRY, 1998, 48 (06) :941-945
[9]   PINOLIDOXIN, A PHYTOTOXIC NONENOLIDE FROM ASCOCHYTA-PINODES [J].
EVIDENTE, A ;
LANZETTA, R ;
CAPASSO, R ;
VURRO, M ;
BOTTALICO, A .
PHYTOCHEMISTRY, 1993, 34 (04) :999-1003
[10]   3 NEW TOXIC PINOLIDOXINS FROM ASCOCHYTA-PINODES [J].
EVIDENTE, A ;
CAPASSO, R ;
ABOUZEID, MA ;
LANZETTA, R ;
VURRO, M ;
BOTTALICO, A .
JOURNAL OF NATURAL PRODUCTS, 1993, 56 (11) :1937-1943