The cis-2-alkyl-3-oxy-tetrahydropyran unit as a building block for new ionophores with C2-symmetry

被引：13

作者：

Carrillo, R ^{[1
]}

Martín, VS ^{[1
]}

Martín, T ^{[1
]}

机构：

[1] Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Spain

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 27期

关键词：

ionophores; lariat ethers; template effect;

D O I：

10.1016/j.tetlet.2004.05.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of cis-2-alkyl-3-oxy-tetrahydropyran unit is reported as a novel structure for the design and synthesis of a new type of ionophore with C-2-symmetry. The synthesis of five macrolides and their complexation properties were investigated. The template effect as an effective tool to improve the selectivity and yield in the macrolactonization process is described. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5215 / 5219

页数：5

共 29 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 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

[3] 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

[4] 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

[5] 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

[6] 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

[7] 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

[8] Synthesis and biological studies of flexible brevetoxin/ciguatoxin models with marked conformational preference [J].

Candenas, ML ;

Pinto, FM ;

Cintado, CG ;

Morales, EQ ;

Brouard, I ;

Díaz, MT ;

Rico, M ;

Rodríguez, E ;

Rodríguez, RM ;

Pérez, R ;

Pérez, RL ;

Martín, JD .

TETRAHEDRON, 2002, 58 (10) :1921-1942

[9] EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES [J].

COREY, EJ ;

NICOLAOU, KC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5614-5616

[10] ENHANCING THE BINDING-PROPERTIES OF A CONFORMATIONALLY RIGID PODAND IONOPHORE [J].

ERICKSON, SD ;

OHLMEYER, MHJ ;

STILL, WC .

TETRAHEDRON LETTERS, 1992, 33 (40) :5925-5928

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