STEREOSPECIFIC SYNTHESIS OF 9-DEMETHYLRETINOIDS VIA PALLADIUM-CATALYZED VINYLBORONIC ACID-VINYL IODIDE CROSS COUPLING

被引：34
作者：
DELERA, AR
TORRADO, A
IGLESIAS, B
LOPEZ, S
机构：
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 41期
关键词：
D O I：
10.1016/S0040-4039(00)60044-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A stereospecific synthesis of 9-demethylretinoids with either trans or 11-cis geometries, based on the thallium-accelerated palladium-catalyzed cross-coupling reactions of an (E)-1-alkenylboronic acid and (E) or (Z)-alkenyl iodides, is described.
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页码：6205 / 6208
页数：4
相关论文
共 24 条
[1]   FORMATION OF Z-1-VINYLIODIDES VIA THE WITTIG REACTION [J].
BESTMANN, HJ ;
RIPPEL, HC ;
DOSTALEK, R .
TETRAHEDRON LETTERS, 1989, 30 (39) :5261-5262
[2]  
BROEK AD, 1983, RECL TRAV CHIM PAY B, V102, P46
[3]   SUBSTRATE SPECIFICITIES AND MECHANISM IN THE ENZYMATIC PROCESSING OF VITAMIN-A INTO 11-CIS-RETINOL [J].
CANADA, FJ ;
LAW, WC ;
RANDO, RR ;
YAMAMOTO, T ;
DERGUINI, F ;
NAKANISHI, K .
BIOCHEMISTRY, 1990, 29 (41) :9690-9697
[4]  
Dawson M. I., 1990, CHEM BIOL SYNTHETIC, DOI [10.1201/9781351070638, DOI 10.1201/9781351070638]
[5]   REMOVAL OF THE 9-METHYL GROUP OF RETINAL INHIBITS SIGNAL TRANSDUCTION IN THE VISUAL PROCESS - A FOURIER-TRANSFORM INFRARED AND BIOCHEMICAL INVESTIGATION [J].
GANTER, UM ;
SCHMID, ED ;
PEREZSALA, D ;
RANDO, RR ;
SIEBERT, F .
BIOCHEMISTRY, 1989, 28 (14) :5954-5962
[6]   REMOVAL OF METHYL-GROUPS FROM RETINAL CONTROLS THE ACTIVITY OF BACTERIORHODOPSIN [J].
GARTNER, W ;
TOWNER, P ;
HOPF, H ;
OESTERHELT, D .
BIOCHEMISTRY, 1983, 22 (11) :2637-2644
[7]   A CONVENIENT SYNTHESIS OF 1-BROMOOLEFINS AND ACETYLENES BY A CHAIN EXTENSION OF ALDEHYDES [J].
MATSUMOTO, M ;
KURODA, K .
TETRAHEDRON LETTERS, 1980, 21 (41) :4021-4024
[8]   NEW STEREOSPECIFIC CROSS-COUPLING BY THE PALLADIUM-CATALYZED REACTION OF 1-ALKENYLBORANES WITH 1-ALKENYL OR 1-ALKYNYL HALIDES [J].
MIYAURA, N ;
YAMADA, K ;
SUZUKI, A .
TETRAHEDRON LETTERS, 1979, 20 (36) :3437-3440
[9]   A STEREOSPECIFIC SYNTHESIS OF CONJUGATED (E,Z)-ALKADIENES AND (Z,Z)-ALKADIENES BY A PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH 1-ALKENYL BROMIDES [J].
MIYAURA, N ;
SUGINOME, H ;
SUZUKI, A .
TETRAHEDRON LETTERS, 1981, 22 (02) :127-130
[10]   NOVEL AND CONVENIENT METHOD FOR THE STEROSPECIFIC AND REGIOSPECIFIC SYNTHESIS OF CONJUGATED ALKADIENES AND ALKENYNES VIA THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH BROMOALKENES AND BROMOALKYNES [J].
MIYAURA, N ;
YAMADA, K ;
SUGINOME, H ;
SUZUKI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (04) :972-980
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