An expedient stereocontrolled synthesis of 7-CIS-retinoids

被引：9

作者：

Alvarez, R ^{[1
]}

Domínguez, B ^{[1
]}

de Lera, AR ^{[1
]}

机构：

[1] Univ Vigo, Dept Quim Organ, Vigo 36200, Spain

来源：

SYNTHETIC COMMUNICATIONS | 2001年 / 31卷 / 13期

关键词：

D O I：

10.1081/SCC-100104430

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Ethyl (7Z)-retinoate 5 has been efficiently synthesized using as key step the Suzuki coupling of an in situ generated alkenylboronic acid and the geometrically homogeneous tetraenyliodide with (Z)-geometry, itself obtained by yodomethylenation according to Stork's conditions. Functional group manipulation then afforded (7Z)-retinal 7.

引用

收藏

页码：2083 / 2087

页数：5

相关论文

共 19 条

[1]

NEW GEOMETRIC ISOMERS OF VITAMIN-A AND OTHER CAROTENOIDS .2. 7-CIS,9-CIS-RETINAL AND 7-CIS,9-CIS,13-CIS-RETINAL - STEREOSELECTIVE SYNTHESIS OF 7-CIS,9-CIS-BETA-IONYLIDENEACETALDEHYDE [J].

ASATO, AE ;

LIU, RSH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (14) :4128-4130

[2]

7-CIS,9-CIS,11-CIS-RETINAL, ALL-CIS-VITAMIN-A, AND "7-CIS,9-CIS,11-CIS-12-FLUORORETINAL - NEW GEOMETRIC ISOMERS OF VITAMIN-A AND CAROTENOIDS .12. [J].

ASATO, AE ;

KINI, A ;

DENNY, M ;

LIU, RSH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2923-2924

[3]

7-CIS-3-DEYDRORETINAL AND 7,9-DICIS-3-DEHYDRORETINAL - HINDERED ISOMERS OF VITAMIN-A(2) ALDEHYDE [J].

CHEN, RL ;

LIU, RSH .

TETRAHEDRON LETTERS, 1994, 35 (34) :6251-6254

[4]

New hindered isomers of 3-dehydroretinal (vitamin A(2)) [J].

Chen, RL ;

Liu, RSH .

TETRAHEDRON, 1996, 52 (23) :7809-7816

[5]

Dawson Marcia I., 1994, P5

[6]

PHOTOCHEMISTRY AND SYNTHESIS OF STEREOISOMERS OF VITAMIN-A [J].

LIU, RSH ;

ASATO, AE .

TETRAHEDRON, 1984, 40 (11) :1931-1969

[7]

PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORONIC ACIDS WITH ORGANIC ELECTROPHILES [J].

MARTIN, AR ;

YANG, YH .

ACTA CHEMICA SCANDINAVICA, 1993, 47 (03) :221-230

[8]

SULFONE ROUTES TO STERICALLY HINDERED 7-CIS ISOMERS OF VITAMIN-A - NEW GEOMETRIC ISOMERS OF VITAMIN-A AND CAROTENOIDS .10. [J].

MILLER, D ;

TRAMMELL, M ;

KINI, A ;

LIU, RSH .

TETRAHEDRON LETTERS, 1981, 22 (05) :409-412

[9]

PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].

MIYAURA, N ;

SUZUKI, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483

[10]

HINDERED CIS ISOMERS OF VITAMIN-A AND RETINENE - THE STRUCTURE OF THE NEO-B ISOMER [J].

OROSHNIK, W ;

BROWN, PK ;

HUBBARD, R ;

WALD, G .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1956, 42 (09) :578-580