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

[61] SAURAT JH, 1985, RETINOIDS NEW TRENDS
[62] SHERMAN MI, 1986, RETINOIDS CELL DIFFE
[63] ALDEHYDE ENOL ESTERS AS NOVEL CHAIN TERMINATORS IN CATIONIC OLEFIN CYCLIZATIONS
SIMMONS, DP
REICHLIN, D
SKUY, D
[J]. HELVETICA CHIMICA ACTA, 1988, 71 (05) : 1000 - 1004
[64] SYNTHESIS OF NEW AROMATIC RETINOID ANALOGS BY LOW-VALENT TITANIUM INDUCED REDUCTIVE ELIMINATION
SOLLADIE, G
GIRARDIN, A
LANG, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) : 2620 - 2628
[65] HIGHLY STEREOSELECTIVE SYNTHESIS OF VITAMIN-A AND ALL-TRANS RETINOIC ACID BY LOW-VALENT TITANIUM INDUCED REDUCTIVE ELIMINATION
SOLLADIE, G
GIRARDIN, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (02) : 213 - 216
[66] HIGHLY STEREOSELECTIVE SYNTHESIS OF 13-CIS RETINOIC ACID BY LOW-VALENT TITANIUM INDUCED REDUCTIVE ELIMINATION
SOLLADIE, G
GIRARDIN, A
METRA, P
[J]. TETRAHEDRON LETTERS, 1988, 29 (02) : 209 - 212
[67] SOLLADIE G, 1993, B SOC CHIM FR, V130, P568
[68] Sporn M.B., 1993, RETINOIDS BIOL CHEM, Vsecond
[69] SPORN MB, 1984, RETINOIDS, V1
[70] SPORN MB, 1984, RETINOIDS, V2

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