CHIRAL SYNTHETIC MACRODIOLIDE AND MACROTRIOLIDE IONOPHORES WITH C2-SYMMETRY AND C3-SYMMETRY

被引:12
作者
BURKE, SD [1 ]
PORTER, WJ [1 ]
RANCOURT, J [1 ]
KALTENBACH, RF [1 ]
机构
[1] UNIV S CAROLINA,DEPT CHEM,COLUMBIA,SC 29208
关键词
D O I
10.1016/S0040-4039(00)98051-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Macrodiolide and macrotriolide synthetic ionophores 7 and 12 have been prepared from hydropyran subunits. Ion binding data and crystallographic analyses for this new class of optically pure macrocyclic hosts are reported. Macrodiolide 7 shows moderate selectivity for Li, with an association constant (Ka) of 1.5 x 105 M-1. © 1990.
引用
收藏
页码:5285 / 5288
页数:4
相关论文
共 25 条
[1]   PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].
BODEN, EP ;
KECK, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395
[2]   THE ESTER ENOLATE CLAISEN REARRANGEMENT - SYNTHESIS OF A C(1)-C(6) ERYTHRONOLIDE FRAGMENT [J].
BURKE, SD ;
SCHOENEN, FJ ;
MURTIASHAW, CW .
TETRAHEDRON LETTERS, 1986, 27 (04) :449-452
[3]   AN ENOLATE CLAISEN ROUTE TO C-PYRANOSIDES - DEVELOPMENT AND APPLICATION TO AN IONOPHORE SYNTHON [J].
BURKE, SD ;
ARMISTEAD, DM ;
SCHOENEN, FJ ;
FEVIG, JM .
TETRAHEDRON, 1986, 42 (11) :2787-2801
[4]   THE DIOXANONE-TO-DIHYDROPYRAN CLAISEN REARRANGEMENT - SYNTHESIS OF C(7)-C(13) FRAGMENTS OF ERYTHRONOLIDE-A AND ERYTHRONOLIDE-B [J].
BURKE, SD ;
SCHOENEN, FJ ;
NAIR, MS .
TETRAHEDRON LETTERS, 1987, 28 (36) :4143-4146
[5]   NOT THE ENOLATE CLAISEN REARRANGEMENT - A SURPRISING ROUTE TO THE RIGHT-WING OF INDANOMYCIN (X-14547A) [J].
BURKE, SD ;
ARMISTEAD, DM ;
SHANKARAN, K .
TETRAHEDRON LETTERS, 1986, 27 (52) :6295-6298
[6]  
COREY EJ, 1976, TETRAHEDRON LETT, V38, P3409
[7]   THE DESIGN OF MOLECULAR HOSTS, GUESTS, AND THEIR COMPLEXES (NOBEL LECTURE) [J].
CRAM, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (08) :1009-1020
[8]  
GERDIL R, 1987, TOP CURR CHEM, V140, P71
[9]  
HASSNER A, 1978, TETRAHEDRON LETT, V46, P4475
[10]   HOST-GUEST COMPLEXATION .18. EFFECTS ON CATION BINDING OF CONVERGENT LIGAND SITES APPENDED TO MACROCYCLIC POLYETHERS [J].
HELGESON, RC ;
WEISMAN, GR ;
TONER, JL ;
TARNOWSKI, TL ;
CHAO, Y ;
MAYER, JM ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4928-4941