CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF (14R)-14-HYDROXY-4,14-RETRO-RETINOL FROM RETINYL ACETATE

被引：7

作者：

COREY, EJ

NOE, MC

GUZMANPEREZ, A

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 24期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(95)00774-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient synthesis of the biologically important vitamin A-derived retinoid (14R)-14-hydroxy-4,14-retro-retinol (1) from retinyl acetate in four steps is described.

引用

页码：4171 / 4174

页数：4

共 14 条

[1] RETINOL IS ESSENTIAL FOR GROWTH OF ACTIVATED HUMAN B-CELLS
BUCK, J
RITTER, G
DANNECKER, L
KATTA, V
COHEN, SL
CHAIT, BT
HAMMERLING, U
[J]. JOURNAL OF EXPERIMENTAL MEDICINE, 1990, 171 (05) : 1613 - 1624
[2] INTRACELLULAR SIGNALING BY 14-HYDROXY-4,14-RETRO-RETINOL
BUCK, J
DERGUINI, F
LEVI, E
NAKANISHI, K
HAMMERLING, U
[J]. SCIENCE, 1991, 254 (5038) : 1654 - 1656
[3] ANHYDRORETINOL - A NATURALLY-OCCURRING INHIBITOR OF LYMPHOCYTE PHYSIOLOGY
BUCK, J
GRUN, F
DERGUINI, F
CHEN, Y
KIMURA, S
NOY, N
HAMMERLING, U
[J]. JOURNAL OF EXPERIMENTAL MEDICINE, 1993, 178 (02) : 675 - 680
[4] DIFFERENCES IN THE ACTION AND METABOLISM BETWEEN RETINOL AND RETINOIC ACID IN LYMPHOCYTES-B
BUCK, J
MYC, A
GARBE, A
CATHOMAS, G
[J]. JOURNAL OF CELL BIOLOGY, 1991, 115 (03) : 851 - 859
[5] SHORT ENANTIOSELECTIVE SYNTHESIS OF (-)-OVALICIN, A POTENT INHIBITOR OF ANGIOGENESIS, USING SUBSTRATE-ENHANCED CATALYTIC ASYMMETRIC DIHYDROXYLATION
COREY, EJ
GUZMANPEREZ, A
NOE, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) : 12109 - 12110
[6] A MECHANISTICALLY DESIGNED MONO-CINCHONA ALKALOID IS AN EXCELLENT CATALYST FOR THE ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS
COREY, EJ
NOE, MC
GROGAN, MJ
[J]. TETRAHEDRON LETTERS, 1994, 35 (35) : 6427 - 6430
[7] RIGID AND HIGHLY ENANTIOSELECTIVE CATALYST FOR THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE CLARIFIES THE ORIGIN OF ENANTIOSPECIFICITY
COREY, EJ
NOE, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) : 12579 - 12580
[8] THE ORIGIN OF HIGH ENANTIOSELECTIVITY IN THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE AND CINCHONA ALKALOID CATALYSTS
COREY, EJ
NOE, MC
SARSHAR, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) : 3828 - 3829
[9] X-RAY CRYSTALLOGRAPHIC STUDIES PROVIDE ADDITIONAL EVIDENCE THAT AN ENZYME-LIKE BINDING POCKET IS CRUCIAL TO THE ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS BY OSO4-BIS-CINCHONA ALKALOID COMPLEXES
COREY, EJ
NOE, MC
SARSHAR, S
[J]. TETRAHEDRON LETTERS, 1994, 35 (18) : 2861 - 2864
[10] INTRACELLULAR SIGNALING ACTIVITY OF SYNTHETIC (14R)-14-HYDROXY-4,14-RETRO-RETINOL, (14S)-14-HYDROXY-4,14-RETRO-RETINOL, AND (14RS)-14-HYDROXY-4,14-RETRO-RETINOL
DERGUINI, F
NAKANISHI, K
HAMMERLING, U
BUCK, J
[J]. BIOCHEMISTRY, 1994, 33 (03) : 623 - 628

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