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：76

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

来源：

TETRAHEDRON | 1995年 / 51卷 / 08期

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

页码：2435 / 2454

页数：20

共 89 条

[1] [Anonymous], 1982, EUR J BIOCHEM, V129, P1
[2] A [3+2] NITRILE OXIDE CYCLO-ADDITION APPROACH TO RETINOIDS
BARALDI, PG
BARCO, A
BENETTI, S
GUARNERI, M
MANFREDINI, S
POLLINI, GP
SIMONI, D
[J]. TETRAHEDRON LETTERS, 1988, 29 (11) : 1307 - 1310
[3] BARALDI PG, 1987, SYNTHESIS-STUTTGART, P857
[4] FORMATION OF Z-1-VINYLIODIDES VIA THE WITTIG REACTION
BESTMANN, HJ
RIPPEL, HC
DOSTALEK, R
[J]. TETRAHEDRON LETTERS, 1989, 30 (39) : 5261 - 5262
[5] PHOTOPHYSICS OF LIGHT TRANSDUCTION IN RHODOPSIN AND BACTERIORHODOPSIN
BIRGE, RR
[J]. 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
BLATZ, PE
LIN, M
BALASUBRAMANIYAN, P
BALASUBRAMANIYAN, V
DEWHURST, PB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (21) : 5930 - +
[7] TRANSPORT AND STORAGE OF VITAMIN-A
BLOMHOFF, R
GREEN, MH
BERG, T
NORUM, KR
[J]. SCIENCE, 1990, 250 (4979) : 399 - 404
[8] STRUCTURAL ASSIGNMENT OF ISOMERIC CHAIN DEMETHYLATED RETINALS BY H-1-NMR SPECTROSCOPY
BROEK, AD
COURTIN, JML
MELLEMA, JR
LUGTENBURG, J
NICOLAY, K
DIJKSTRA, K
KAPTEIN, R
[J]. 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
BROWN, HC
HAMAOKA, T
RAVINDRA.N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (17) : 5786 - 5788

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