Synthesis of highly functionalized γ-lactones via 1,5-electrocyclic ring closure

被引:13
作者
Anac, Olca [1 ]
Gungor, F. Seyma [1 ]
Merey, Gokce [1 ]
机构
[1] Tech Univ Istanbul, Fac Sci & Letters, Dept Chem, TR-34469 Istanbul, Turkey
关键词
D O I
10.1002/hlca.200690120
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have investigated 1,5-electrocyclic ring-closure reactions of conjugated esters with dimethyl diazomalonate in the presence of [Cu(acac)(2)] as catalyst. Our new protocol offers an easy entry to various polyfunctionalized gamma-lactones in high yields. Their subsequent derivatives may be used as valuable intermediates, especially in the synthesis of natural products and their analogues.
引用
收藏
页码:1231 / 1240
页数:10
相关论文
共 38 条
[1]  
Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO
[2]  
2-E
[3]   EFFECT OF CATALYST ON ZWITTERIONIC INTERMEDIACY IN ADDITIONS OF DIMETHYL DIAZOMALONATE TO VINYL ETHERS [J].
ALONSO, ME ;
FERNANDEZ, R .
TETRAHEDRON, 1989, 45 (11) :3313-3320
[4]   TRANSITION-METAL-CATALYZED REACTIONS OF UNSATURATED ALPHA-DIAZO-ALPHA-(TRIMETHYLSILYL)ACETATES WITH CARBONYL-COMPOUNDS [J].
ALT, M ;
MAAS, G .
CHEMISCHE BERICHTE, 1994, 127 (08) :1537-1542
[5]   TRANSITION-METAL-CATALYZED DECOMPOSITION OF DIAZO(TRIALKYLSILYL)-ACETATES - INTERMOLECULAR FORMATION AND TRAPPING OF CARBONYL YLIDES [J].
ALT, M ;
MAAS, G .
TETRAHEDRON, 1994, 50 (25) :7435-7444
[6]   Reactions of α,β-enones with diazo compounds part 3 on the nature of the 1,5-ring closure of α,β-enone ylides [J].
Anaç, O ;
Özdemir, AD ;
Sezer, Ö .
HELVETICA CHIMICA ACTA, 2003, 86 (02) :290-298
[7]   Reactions of α,β-enones with diazo compounds -: Part 4.: Reaction pathways from (Z)- and (E)-α,β-enones with dimethyl diazomalonate [J].
Anaç, O ;
Güngör, FS ;
Kahveci, Ç ;
Cansever, MS .
HELVETICA CHIMICA ACTA, 2004, 87 (02) :408-415
[8]  
Anac O, 1997, LIEBIGS ANN-RECL, P1249
[9]  
ANAC O, 2002, Z KRIST-NEW CRYST ST, V217, P609
[10]   Effects of solvents and water in Ti(III)-mediated radical cyclizations of epoxygermacrolides.: Straightforward synthesis and absolute stereochemistry of (+)-3α-hydroxyreynosin and related eudesmanolides [J].
Barrero, AF ;
Oltra, JE ;
Cuerva, JM ;
Rosales, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2566-2571