THE SYNTHESIS OF DL-3,3-DIFLUOROGLUTAMIC ACID FROM A 3-OXOPROLINOL DERIVATIVE

被引：30

作者：

HART, BP

COWARD, JK

机构：

[1] UNIV MICHIGAN,DEPT CHEM,ANN ARBOR,MI 48109

[2] UNIV MICHIGAN,COLL PHARM,INTERDEPT PROGRAM MED CHEM,ANN ARBOR,MI 48109

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)74045-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DL-3,3-Difluoroglutamic acid was synthesized from a masked 3-hydroxyprolinol, 6-hydroxy-l-aza-3-oxabicyclo[3.3.0]octan-2-one, in eight steps. The described synthetic route expands the utility of fluoroproline derivatives as precursors of fluoroglutamic acids.

引用

页码：4917 / 4920

页数：4

共 11 条

[1] 3-PYRROLIDINONES BY INTRAMOLECULAR CONDENSATION
BLAKE, J
RAPOPORT, H
WILLSON, CD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (23) : 5293 - &
[2] COWARD JK, 1991, SELECTIVE FLUORINATI, P196
[3] HART BT, UNPUB
[4] OXIDATION OF STERICALLY HINDERED ALCOHOLS TO CARBONYLS WITH DIMETHYL SULFOXIDE-TRIFLUOROACETIC ANHYDRIDE
HUANG, SL
OMURA, K
SWERN, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (20) : 3329 - 3331
[5] NEW STEREOSPECIFIC SYNTHESES AND X-RAY-DIFFRACTION STRUCTURES OF (-)-D-ERYTHRO-4-FLUOROGLUTAMIC AND (+)-L-THREO-4-FLUOROGLUTAMIC ACID
HUDLICKY, M
MEROLA, JS
[J]. TETRAHEDRON LETTERS, 1990, 31 (51) : 7403 - 7406
[6] METABOLISM OF THE DIAMINOANTIFOLATES - BIOSYNTHESIS AND PHARMACOLOGY OF THE 7-HYDROXYL AND POLYGLUTAMYL METABOLITES OF METHOTREXATE AND RELATED ANTIFOLATES
MATHERLY, LH
SEITHER, RL
GOLDMAN, ID
[J]. PHARMACOLOGY & THERAPEUTICS, 1987, 35 (1-2) : 27 - 56
[7] MCGUIRE JJ, 1990, J BIOL CHEM, V265, P14073
[8] MCGUIRE JJ, 1985, J BIOL CHEM, V260, P6747
[9] MCGUIRE JJ, 1989, CANCER RES, V49, P4517
[10] STEREOSELECTIVE INTRAMOLECULAR HALOAMIDATION OF N-PROTECTED 3-HYDROXY-4-PENTENYLAMINES AND 4-HYDROXY-5-HEXENYLAMINES
TAMARU, Y
KAWAMURA, S
BANDO, T
TANAKA, K
HOJO, M
YOSHIDA, Z
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) : 5491 - 5501

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