Resolution of a citric acid derivative: synthesis of (R)-(-)-homocitric acid-gamma-lactone

被引：20

作者：

Ancliff, RA

Russell, AT

Sanderson, AJ

机构：

[1] UNIV SALFORD,DEPT CHEM,SALFORD M5 4WT,LANCS,ENGLAND

[2] GLAXO WELLCOME RES & DEV LTD,MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 20期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0957-4166(97)00435-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in greater than or equal to 90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-alpha-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)-homocitric acid utilising an Arndt-Eistert homologation followed by acid catalysed deprotection. (C) 1997 Elsevier Science Ltd.

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页码：3379 / 3382

页数：4

相关论文

共 11 条

[1] Total synthesis of rhizoferrin, an iron chelator [J].

Bergeron, RJ ;

Xin, MG ;

Smith, RE ;

Wollenweber, M ;

McManis, JS ;

Ludin, C ;

Abboud, KA .

TETRAHEDRON, 1997, 53 (02) :427-434

[2] ASYMMETRIC-SYNTHESIS OF MACBECIN-I [J].

EVANS, DA ;

MILLER, SJ ;

ENNIS, MD ;

ORNSTEIN, PL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1067-1069

[3] ASYMMETRIC-SYNTHESIS OF THE BENZOQUINOID ANSAMYCIN ANTITUMOR ANTIBIOTICS - TOTAL SYNTHESIS OF (+)-MACBECIN [J].

EVANS, DA ;

MILLER, SJ ;

ENNIS, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :471-485

[4] NATURAL FERRIC IONOPHORES - TOTAL SYNTHESIS OF SCHIZOKINEN, SCHIZOKINEN-A, AND ARTHROBACTIN [J].

LEE, BH ;

MILLER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (01) :24-31

[5]

MARAGOUDAKIS ME, 1966, J BIOL CHEM, V241, P695

[6] Methylene-citric anhydride - The aniline derivatives of citric and aconitic acids [J].

Nau, CA ;

Brown, EB ;

Bailey, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1925, 47 :2596-2606

[7] INTERPRETATION OF EXPERIMENTS ON METABOLIC PROCESSES, USING ISOTOPIC TRACER ELEMENTS [J].

OGSTON, AG .

NATURE, 1948, 162 (4129) :963-963

[8] Enantioselective syntheses of (-)- and (+)-homocitric acid lactones [J].

Rodriguez, GH ;

Biellmann, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1822-1824

[9] ABSOLUTE CONFIGURATION OF HOMOCITRIC ACID (2-HYDROXY-1,2,4-BUTANETRICARBOXYLIC ACID) AN INTERMEDIATE IN LYSINE BIOSYNTHESIS [J].

THOMAS, U ;

KALYANPUR, MG ;

STEVENS, CM .

BIOCHEMISTRY, 1966, 5 (08) :2513-+

[10] The design and synthesis of nucleoside triphosphate isosteres as potential inhibitors of HIV reverse transcriptase [J].

Weaver, R ;

Gilbert, IH .

TETRAHEDRON, 1997, 53 (15) :5537-5562