PREPARATIVE SEPARATION OF THE DIASTEREOISOMERS OF DIOXINDOLYL-L-ALANINE AND ASSIGNMENT OF STEREOCHEMISTRY AT C-3

被引:77
作者
LABROO, RB [1 ]
COHEN, LA [1 ]
机构
[1] NIDDKD, BIOORGAN CHEM LAB, BETHESDA, MD 20892 USA
关键词
D O I
10.1021/jo00303a027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The diastereoisomers of dioxindolyl-L-alanine are obtained in a 1:1 ratio by air oxidation of oxindolyl-L-alanine. Preparative separation of the diastereoisomers is achieved by reverse-phase HPLC. Stereochemistry of the hydroxyl group at C-3 is assigned by transformation to a related pair of diastereoisomers of known stereochemistry. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:4901 / 4904
页数:4
相关论文
共 17 条
[1]   TOTAL SYNTHESIS OF TRYPTOQUIVALINE-G [J].
BUCHI, G ;
DESHONG, PR ;
KATSUMURA, S ;
SUGIMURA, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :5084-5086
[2]   STUDIES IN THE INDOLE SERIES .16. OXINDOLE-3-ALANINE AND DIOXINDOLE-3-ALANINE [J].
JULIAN, PL ;
DAILEY, EE ;
PRINTY, HC ;
COHEN, HL ;
HAMASHIGE, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (14) :3503-3508
[3]  
LABROO RB, UNPUB
[4]  
LABROO RB, 1990, THESIS G WASHINGTON
[5]   AMINO GROUP BLOCKING - IMPROVED METHOD FOR N-PHTHALOYLATION USING N-(ETHOXYCARBONYL)PHTHALIMIDE [J].
MCARTHUR, CR ;
WORSTER, PM ;
OKON, AU .
SYNTHETIC COMMUNICATIONS, 1983, 13 (04) :311-318
[6]   Optical activity in the indole group [J].
McKenzie, A ;
Stewart, PA .
JOURNAL OF THE CHEMICAL SOCIETY, 1935, :104-111
[7]  
NAGASAKA T, 1971, CHEM PHARM BULL, V19, P603
[8]   REVERSED-PHASE LIQUID-CHROMATOGRAPHIC RESOLUTION OF AMINO-ACID ENANTIOMERS BY DERIVATIZATION WITH 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE [J].
NIMURA, N ;
OGURA, H ;
KINOSHITA, T .
JOURNAL OF CHROMATOGRAPHY, 1980, 202 (03) :375-379
[9]   NEW, PRACTICAL SYNTHESIS OF L-2-HYDROXYTRYPTOPHAN AND ITS DERIVATIVES [J].
OHNO, M ;
SPANDE, TF ;
WITKOP, B .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (17) :2635-2637
[10]  
OHNUMA T, 1982, HETEROCYCLES, V17, P377