2 CHIRAL SYNTHESES OF THREO-3-HYDROXYLYSINE

被引：56

作者：

HUGHES, PF

SMITH, SH

OLSON, JT

机构：

[1] Sphinx Pharmaceuticals Inc., Five University Place, Durham

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 19期

关键词：

D O I：

10.1021/jo00098a047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two efficient chiral syntheses of 3-hydroxylysine, a naturally occurring amino acid and a putative intermediate in the synthesis of balanol, a potent protein kinase C inhibitor, are described. The synthesis of (2R,3S)-3-hydroxylysine utilizes Hayashi's chiral ferroceno gold catalyst. The synthesis of (2S,3R)-3-hydroxylysine demonstrates a beta-hydroxy amino acid synthesis with the chirality derived from the Sharpless chiral cis-hydroxylation.

引用

页码：5799 / 5802

页数：4

共 17 条

[1] SYNTHESES AND CRYSTAL-STRUCTURES OF THE CINCHONA ALKALOID DERIVATIVES USED AS LIGANDS IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS
AMBERG, W
BENNANI, YL
CHADHA, RK
CRISPINO, GA
DAVIS, WD
HARTUNG, J
JEONG, KS
OGINO, Y
SHIBATA, T
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) : 844 - 849
[2] BONATI F, 1973, GAZZ CHIM ITAL, V103, P373
[3] STUDIES ON THE FUNGAL PHYTOTOXIN VICTORIN - STRUCTURES OF 3 NOVEL AMINO-ACIDS FROM THE ACID HYDROLYZATE
GLOER, JB
MEINWALD, J
WALTON, JD
EARLE, ED
[J]. EXPERIENTIA, 1985, 41 (11): : 1370 - 1374
[4] A CONVENIENT SYNTHESIS OF N-PROTECTED DIPHENYL PHOSPHONATE ESTER ANALOGS OF ORNITHINE, LYSINE AND HOMOLYSINE
HAMILTON, R
WALKER, BJ
WALKER, B
[J]. TETRAHEDRON LETTERS, 1993, 34 (17) : 2847 - 2850
[5] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION METAL-COMPLEXES .1. PREPARATION OF CHIRAL FERROCENYLPHOSPHINES
HAYASHI, T
MISE, T
FUKUSHIMA, M
KAGOTANI, M
NAGASHIMA, N
HAMADA, Y
MATSUMOTO, A
KAWAKAMI, S
KONISHI, M
YAMAMOTO, K
KUMADA, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) : 1138 - 1151
[6] SILVER(I)-CATALYZED ASYMMETRIC ALDOL REACTION OF ISOCYANOACETATE
HAYASHI, T
UOZUMI, Y
YAMAZAKI, A
SAWAMURA, M
HAMASHIMA, H
ITO, Y
[J]. TETRAHEDRON LETTERS, 1991, 32 (24) : 2799 - 2802
[7] ASYMMETRIC-SYNTHESIS OF THREO-SPHINGOSINES AND ERYTHRO-SPHINGOSINES BY ASYMMETRIC ALDOL REACTION OF ALPHA-ISOCYANOACETATE CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX
ITO, Y
SAWAMURA, M
HAYASHI, T
[J]. TETRAHEDRON LETTERS, 1988, 29 (02) : 239 - 240
[8] ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY-ALPHA-ALKYLAMINO ACIDS BY ASYMMETRIC ALDOL REACTION OF ALPHA-ISOCYANOCARBOXYLATES CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEXES
ITO, Y
SAWAMURA, M
SHIRAKAWA, E
HAYASHIZAKI, K
HAYASHI, T
[J]. TETRAHEDRON, 1988, 44 (17) : 5253 - 5262
[9] A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES
KOLB, HC
SHARPLESS, KB
[J]. TETRAHEDRON, 1992, 48 (48) : 10515 - 10530
[10] BALANOL - A NOVEL AND POTENT INHIBITOR OF PROTEIN-KINASE-C FROM THE FUNGUS VERTICILLIUM-BALANOIDES
KULANTHAIVEL, P
HALLOCK, YF
BOROS, C
HAMILTON, SM
JANZEN, WP
BALLAS, LM
LOOMIS, CR
JIANG, JB
KATZ, B
STEINER, JR
CLARDY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) : 6452 - 6453

← 1 2 →