THE SUZUKI REACTION IN STEREOCONTROLLED POLYENE SYNTHESIS - RETINOL (VITAMIN-A), ITS 9-DEMETHYL AND/OR 13-DEMETHYL ANALOGS, AND RELATED 9-DEMETHYL-DIHYDRORETINOIDS

被引:77
作者
TORRADO, A [1 ]
IGLESIAS, B [1 ]
LOPEZ, S [1 ]
DELERA, AR [1 ]
机构
[1] UNIV SANTIAGO DE COMPOSTELA, DEPT QUIM ORGAN, E-15706 SANTIAGO, SPAIN
关键词
D O I
10.1016/0040-4020(94)01108-C
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new synthesis of retinol (vitamin A) and 9- and/or 13-demethylretinols, with essentially complete control of regio- and stereochemistry, is described which is based on the thallium-accelerated, palladium-catalyzed cross-coupling reactions of (E)-1-alkenylboronic acids and (E)-1-alkenyl iodides (Suzuki reaction). The procedure has also been extended to the stereocontrolled synthesis of a series of 9-demethyl-dihydroretinoids of potential biological interest.
引用
收藏
页码:2435 / 2454
页数:20
相关论文
共 89 条
[1]  
[Anonymous], 1982, EUR J BIOCHEM, V129, P1
[2]   A [3+2] NITRILE OXIDE CYCLO-ADDITION APPROACH TO RETINOIDS [J].
BARALDI, PG ;
BARCO, A ;
BENETTI, S ;
GUARNERI, M ;
MANFREDINI, S ;
POLLINI, GP ;
SIMONI, D .
TETRAHEDRON LETTERS, 1988, 29 (11) :1307-1310
[3]  
BARALDI PG, 1987, SYNTHESIS-STUTTGART, P857
[4]   FORMATION OF Z-1-VINYLIODIDES VIA THE WITTIG REACTION [J].
BESTMANN, HJ ;
RIPPEL, HC ;
DOSTALEK, R .
TETRAHEDRON LETTERS, 1989, 30 (39) :5261-5262
[5]   PHOTOPHYSICS OF LIGHT TRANSDUCTION IN RHODOPSIN AND BACTERIORHODOPSIN [J].
BIRGE, RR .
ANNUAL REVIEW OF BIOPHYSICS AND BIOENGINEERING, 1981, 10 :315-354
[6]   A NEW SERIES OF SYNTHETIC VISUAL PIGMENTS FROM CATTLE OPSIN AND HOMOLOGS OF RETINAL [J].
BLATZ, PE ;
LIN, M ;
BALASUBRAMANIYAN, P ;
BALASUBRAMANIYAN, V ;
DEWHURST, PB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (21) :5930-+
[7]   TRANSPORT AND STORAGE OF VITAMIN-A [J].
BLOMHOFF, R ;
GREEN, MH ;
BERG, T ;
NORUM, KR .
SCIENCE, 1990, 250 (4979) :399-404
[8]   STRUCTURAL ASSIGNMENT OF ISOMERIC CHAIN DEMETHYLATED RETINALS BY H-1-NMR SPECTROSCOPY [J].
BROEK, AD ;
COURTIN, JML ;
MELLEMA, JR ;
LUGTENBURG, J ;
NICOLAY, K ;
DIJKSTRA, K ;
KAPTEIN, R .
ORGANIC MAGNETIC RESONANCE, 1982, 19 (02) :105-107
[9]  
BROEK AD, 1983, RECL TRAV CHIM PAY B, V102, P46
[10]   REACTION OF ALKENYLBORONIC ACIDS WITH IODINE UNDER INFLUENCE OF BASE - SIMPLE PROCEDURE FOR STEREOSPECIFIC CONVERSION OF TERMINAL ALKYNES INTO TRANS-1-ALKENYL IODIDES VIA HYDROBORATION [J].
BROWN, HC ;
HAMAOKA, T ;
RAVINDRA.N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (17) :5786-5788