Dienolether condensations -: a powerful tool in carotenoid synthesis

被引:10
作者
Rüttimann, A [1 ]
机构
[1] F Hoffmann La Roche & Co Ltd, Chem Proc Technol Vitamins & Fine Chem Div, CH-4070 Basel, Switzerland
关键词
D O I
10.1351/pac199971122285
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The catalytic dienolether condensation reactions, discovered by Nazarov and Makin in 1958, are of special interest in the carotenoid field for chain extension by five carbon atoms. In this paper, new developments in the synthesis of apoesters and apocarotenals using vinyl ketene acetals and dienolethers, respectively, as C-5-building blocks are discussed. New 'Wittig-free' routes to astaxanthin and canthaxanthin applying these Lewis acid-catalysed dienolether condensation reactions are described.
引用
收藏
页码:2285 / 2293
页数:9
相关论文
共 19 条
[1]   SYNTHESIS OF CAROTINOIDS OVER SULFONES - SYNTHESIS OF APOCAROTINOIDS AND TORULARHODIN ESTER [J].
FISCHLI, A ;
MAYER, H .
HELVETICA CHIMICA ACTA, 1975, 58 (05) :1492-1497
[2]  
FLEMING I, 1979, TETRAHEDRON LETT, V34, P3205
[3]   SYNTHESEN IN DER CAROTINOID-REIHE .1. DIE TECHNISCHE SYNTHESE VON BETA-CAROTIN [J].
ISLER, O ;
LINDLAR, H ;
MONTAVON, M ;
RUEGG, R ;
ZELLER, P .
HELVETICA CHIMICA ACTA, 1956, 39 (01) :249-&
[4]  
KLAUI H, 1981, CAROTENOIDS COLORANT, P48
[5]  
LABLER L, 1996, SYNTHESIS 1, V2, P27
[6]   ENOL ETHER SYNTHESIS OF POLYENES [J].
MAKIN, SM .
PURE AND APPLIED CHEMISTRY, 1976, 47 (2-3) :173-181
[7]  
MAKIN SM, 1962, J GEN CHEM USSR, V32, P3112
[8]  
MAKIN SM, 1961, J GEN CHEM USSR, V31, P3096
[9]  
MARUSICH WL, 1981, CAROTENOIDS COLORANT, P320
[10]  
MULLERCUNRADI M, 1939, Patent No. 2165962