A NEW SYNTHETIC ROUTE TO MACROCYCLES - SYNTHESIS OF LARGE RING ENAMINOLACTONES

被引:10
作者
JOURDAIN, F [1 ]
POMMELET, JC [1 ]
机构
[1] UNIV CAEN,ISMRA,CNRS,COMPOSES THIOORGAN LAB,F-14050 CAEN,FRANCE
关键词
D O I
10.1016/S0040-4039(00)76754-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Macrocyclic enaminolactones 5 are prepared in three steps from commercialy available chloroalcohols 1. The cyclization step is performed by intramolecular nucleophilic addition of the hydroxy group to an aminomethyleneketene generated by thermolysis.
引用
收藏
页码:1545 / 1548
页数:4
相关论文
共 30 条
[1]   SYNTHESIS OF MACROCYCLIC LACTONES - APPROACHES TO COMPLEX MACROLIDE ANTIBIOTICS [J].
BACK, TG .
TETRAHEDRON, 1977, 33 (23) :3041-3059
[2]   HYDROXY- AND AMINOMETHYLENE MELDRUMS ACIDS (CYCLIC ACYLALS .17. [J].
BIHLMAYER, GA ;
DERFLING.G ;
DERKOSCH, J ;
POLANSKY, OE .
MONATSHEFTE FUR CHEMIE, 1967, 98 (03) :564-+
[3]   TOTAL SYNTHESIS OF COMBRETASTATIN D-2 - INTRAMOLECULAR ULLMANN MACROCYCLIZATION REACTION [J].
BOGER, DL ;
SAKYA, SM ;
YOHANNES, D .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4204-4207
[4]   SYNTHESIS OF AMPHOTERICIN-B .2. FRAGMENT C-D OF THE AGLYCONE [J].
BOSCHELLI, D ;
TAKEMASA, T ;
NISHITANI, Y ;
MASAMUNE, S .
TETRAHEDRON LETTERS, 1985, 26 (43) :5239-5242
[5]   ANTIBIOTICA AUS ACTINOMYCCTEN .6. PIKROMYCIN, EIN BITTER SCHMECKENDES ANTIBIOTICUM AUS ACTINOMYCETEN [J].
BROCKMANN, H ;
HENKEL, W .
CHEMISCHE BERICHTE-RECUEIL, 1951, 84 (03) :284-288
[6]   THERMOLYSIS OF CYCLIC BETA-ENAMINODIESTERS - ACCESS TO VARIOUS BETA-ENAMINOESTERS, BETA-ENAMINOTHIOESTERS AND BETA-ENAMINOAMIDES [J].
CELERIER, JP ;
LHOMMET, G ;
MAITTE, P .
TETRAHEDRON LETTERS, 1981, 22 (10) :963-964
[7]  
CELERIER JP, 1981, SYNTHESIS-STUTTGART, P130
[8]  
CELERIER JP, 1983, SYNTHESIS-STUTTGART, P195
[9]  
CHEIKH AB, 1988, TETRAHEDRON LETT, V29, P5919