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
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
收藏
页码:5799 / 5802
页数:4
相关论文
共 17 条
[1]   SYNTHESES AND CRYSTAL-STRUCTURES OF THE CINCHONA ALKALOID DERIVATIVES USED AS LIGANDS IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].
AMBERG, W ;
BENNANI, YL ;
CHADHA, RK ;
CRISPINO, GA ;
DAVIS, WD ;
HARTUNG, J ;
JEONG, KS ;
OGINO, Y ;
SHIBATA, T ;
SHARPLESS, KB .
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 [J].
GLOER, JB ;
MEINWALD, J ;
WALTON, JD ;
EARLE, ED .
EXPERIENTIA, 1985, 41 (11) :1370-1374
[4]   A CONVENIENT SYNTHESIS OF N-PROTECTED DIPHENYL PHOSPHONATE ESTER ANALOGS OF ORNITHINE, LYSINE AND HOMOLYSINE [J].
HAMILTON, R ;
WALKER, BJ ;
WALKER, B .
TETRAHEDRON LETTERS, 1993, 34 (17) :2847-2850
[5]   ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION METAL-COMPLEXES .1. PREPARATION OF CHIRAL FERROCENYLPHOSPHINES [J].
HAYASHI, T ;
MISE, T ;
FUKUSHIMA, M ;
KAGOTANI, M ;
NAGASHIMA, N ;
HAMADA, Y ;
MATSUMOTO, A ;
KAWAKAMI, S ;
KONISHI, M ;
YAMAMOTO, K ;
KUMADA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) :1138-1151
[6]   SILVER(I)-CATALYZED ASYMMETRIC ALDOL REACTION OF ISOCYANOACETATE [J].
HAYASHI, T ;
UOZUMI, Y ;
YAMAZAKI, A ;
SAWAMURA, M ;
HAMASHIMA, H ;
ITO, Y .
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 [J].
ITO, Y ;
SAWAMURA, M ;
HAYASHI, T .
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 [J].
ITO, Y ;
SAWAMURA, M ;
SHIRAKAWA, E ;
HAYASHIZAKI, K ;
HAYASHI, T .
TETRAHEDRON, 1988, 44 (17) :5253-5262
[9]   A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES [J].
KOLB, HC ;
SHARPLESS, KB .
TETRAHEDRON, 1992, 48 (48) :10515-10530
[10]   BALANOL - A NOVEL AND POTENT INHIBITOR OF PROTEIN-KINASE-C FROM THE FUNGUS VERTICILLIUM-BALANOIDES [J].
KULANTHAIVEL, P ;
HALLOCK, YF ;
BOROS, C ;
HAMILTON, SM ;
JANZEN, WP ;
BALLAS, LM ;
LOOMIS, CR ;
JIANG, JB ;
KATZ, B ;
STEINER, JR ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6452-6453