Synthesis and cation complexation properties of new macrolides

被引:17
作者
Carrillo, R [1 ]
Martín, VS [1 ]
López, M [1 ]
Martín, T [1 ]
机构
[1] Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, San Cristobal la Laguna 38206, Tenerife, Spain
关键词
macrolides; ionophores; template effect;
D O I
10.1016/j.tet.2005.06.034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cis-2-alkyl-3-oxy-tetrahydropyran unit as a novel structure for the design and synthesis of a new type of ionophores with C-2-symmetry is reported. The synthesis of seven different macrolides and a crown ether and their cation complexation properties were investigated. The X-ray crystal structure of some of the receptors provides valuable information on the preferred conformation of tetrahydropyrans in the solid state that can be related to the cation complexation properties in solution. The kinetic template effect has been proved to be a useful tool to improve the yield and selectivity in the synthesis of macrodiolide 3. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8177 / 8191
页数:15
相关论文
共 44 条
[1]   STRUCTURE OF MONENSIC ACID A NEW BIOLOGICALLY ACTIVE COMPOUND [J].
AGTARAP, A ;
CHAMBERLIN, JW ;
PINKERTON, M ;
STEINRAUF, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (22) :5737-+
[2]   The furan approach to oxacycles.: Part 3:: Stereoselective synthesis of 2,3-disubstituted tetrahydropyrans [J].
Alonso, D ;
Pérez, M ;
Gómez, G ;
Covelo, B ;
Fall, Y .
TETRAHEDRON, 2005, 61 (08) :2021-2026
[3]  
Armarego W.L. F., 1996, PURIFICATION LAB CHE, V4th
[4]   PHASE-TRANSFER-CATALYZED SYNTHESIS OF OLIGOETHYLENE GLYCOLS AND DERIVATIVES [J].
BARTSCH, RA ;
CASON, CV ;
CZECH, BP .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) :857-860
[5]   THE ISOLATION OF 3 NEW CRYSTALLINE ANTIBIOTICS FROM STREPTOMYCES [J].
BERGER, J ;
RACHLIN, AI ;
SCOTT, WE ;
STERNBACH, LH ;
GOLDBERG, MW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (11) :5295-5298
[6]   CRYSTAL AND MOLECULAR-STRUCTURE OF FREE ACID FORM OF ANTIBIOTIC X-206 HYDRATE [J].
BLOUNT, JF ;
WESTLEY, JW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (13) :533-533
[7]   INTERACTIONS OF MACROBICYCLIC POLYETHERS WITH IONS AND ION-PAIRS OF PICRATE SALTS [J].
BOURGOIN, M ;
WONG, KH ;
HUI, JY ;
SMID, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (12) :3462-3467
[8]   CHIRAL SYNTHETIC MACRODIOLIDE AND MACROTRIOLIDE IONOPHORES WITH C2-SYMMETRY AND C3-SYMMETRY [J].
BURKE, SD ;
PORTER, WJ ;
RANCOURT, J ;
KALTENBACH, RF .
TETRAHEDRON LETTERS, 1990, 31 (37) :5285-5288
[9]   Cyclic hydropyran oligolides as preorganized ligand arrays: Modular assembly of 18-, 24-, 36-, 48-, 54- and 72-membered rings via iteration and cyclooligomerization [J].
Burke, SD ;
Heap, CR ;
Porter, WJ ;
Song, YT .
TETRAHEDRON LETTERS, 1996, 37 (03) :343-346
[10]   Synthesis and study of C3-symmetric hydropyran cyclooligolides with oriented aryl and alcohol appendages at 10 Å spacing [J].
Burke, SD ;
Zhao, Q .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1489-1500