Enantioselective synthesis of all of the stereoisomers of (E)-13,14-dihydroxyretinol (DHR)

被引：9
作者：
Alvarez, S [1 ]
Alvarez, R [1 ]
de Lera, AR [1 ]
机构：
[1] Univ Vigo, Dept Quim Organ, Vigo 36200, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 05期
关键词：
D O I：
10.1016/j.tetasy.2004.01.019
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The Stille cross-coupling of trienyliodide 4 and E-alkenylstannanes 5, derived from enantioenriched diols obtained by a Sharpless asymmetric dihydroxylation (SAD), provides a convergent route to all stereoisomers of 13,14-dihydroxyretinol (DHR), an immunomodulator derived from vitamin A. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：839 / 846
页数：8
相关论文
共 73 条
[1]   Stereocontrolled synthesis of all-(E)- and (8Z)-anhydroretinol [J].
Alvarez, R ;
Iglesias, B ;
López, S ;
de Lera, AR .
TETRAHEDRON LETTERS, 1998, 39 (31) :5659-5662
[2]  
[Anonymous], 1982, EUR J BIOCHEM, V129, P1
[3]   TOTAL SYNTHESIS OF (+)-MACBECIN-I [J].
BAKER, R ;
CASTRO, JL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01) :47-65
[4]   SELECTIVE ASYMMETRIC DIHYDROXYLATION OF POLYENES [J].
BECKER, H ;
SOLER, MA ;
SHARPLESS, KB .
TETRAHEDRON, 1995, 51 (05) :1345-1376
[5]   An efficient method in stannylcupration of a methyl substituted enyne or alkyne by kinetic control using methanol [J].
Betzer, JF ;
Ardisson, J ;
Lallemand, JY ;
Pancrazi, A .
TETRAHEDRON LETTERS, 1997, 38 (13) :2279-2282
[6]   Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities [J].
Betzer, JF ;
Delaloge, F ;
Muller, B ;
Pancrazi, A ;
Prunet, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7768-7780
[7]  
Bolm C., 2000, Catal. Asymmetric Synth, V2nd, P399
[8]   Nuclear receptor ligand-binding domains three-dimensional structures, molecular interactions and pharmacological implications [J].
Bourguet, W ;
Germain, P ;
Gronemeyer, H .
TRENDS IN PHARMACOLOGICAL SCIENCES, 2000, 21 (10) :381-388
[9]   NON-ENZYMATIC HYDRATION, AMINE ADDITION, AND OXIDATION REACTIONS OF AZA-ARENE OXIDES [J].
BOYD, DR ;
DAVIES, RJH ;
DUNLOP, R ;
PORTER, HP ;
HAMILTON, L ;
MCCULLOUGH, JJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (03) :163-165
[10]   INTRACELLULAR SIGNALING BY 14-HYDROXY-4,14-RETRO-RETINOL [J].
BUCK, J ;
DERGUINI, F ;
LEVI, E ;
NAKANISHI, K ;
HAMMERLING, U .
SCIENCE, 1991, 254 (5038) :1654-1656
12345678