A short highly stereoselective synthesis of the fluorinated natural product (2S,3S)-4-fluorothreonine

被引:14
作者
Amin, MR
Harper, DB
Moloney, JM
Murphy, CD
Howard, JAK
OHagan, D
机构
[1] UNIV DURHAM,SCI LABS,DEPT CHEM,DURHAM DH1 3LE,ENGLAND
[2] QUEENS UNIV BELFAST,DEPT FOOD SCI,BELFAST BT9 5PX,ANTRIM,NORTH IRELAND
关键词
D O I
10.1039/a703121a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A three step stereoselective route to the fluorinated natural product (2S,3S)-4-fluorothreonine is described; the route is amenable to the preparation of (2S,3S)-4-fluoro[3-H-2]threonine and (2S,3R)-[4,4,4-H-2(3)] threonine.
引用
收藏
页码:1471 / 1472
页数:2
相关论文
共 12 条
[1]  
BLASER D, 1991, LIEBIGS ANN CHEM, P1067
[2]   Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. Glycine and pyruvate as precursors [J].
Hamilton, JTG ;
Amin, MR ;
Harper, DB ;
OHagan, D .
CHEMICAL COMMUNICATIONS, 1997, (08) :797-798
[3]   Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. The stereochemical processing of glycerol [J].
Nieschalk, J ;
Hamilton, JTG ;
Murphy, CD ;
Harper, DB ;
OHagan, D .
CHEMICAL COMMUNICATIONS, 1997, (08) :799-800
[4]   EFFICIENT ROUTES TO ISOTOPICALLY LABELED EPICHLOROHYDRINS ((CHLOROMETHYL) OXIRANES) [J].
OHAGAN, D ;
WHITE, J ;
JONES, DA .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1994, 34 (09) :871-880
[5]   BIOSYNTHESIS OF FLUORINATED SECONDARY METABOLITES BY STREPTOMYCES-CATTLEYA [J].
REID, KA ;
HAMILTON, JTG ;
BOWDEN, RD ;
OHAGAN, D ;
DASARADHI, L ;
AMIN, MR ;
HARPER, DB .
MICROBIOLOGY-SGM, 1995, 141 :1385-1393
[6]   BIOSYNTHESIS OF FLUOROTHREONINE AND FLUOROACETIC ACID BY THE THIENAMYCIN PRODUCER, STREPTOMYCES-CATTLEYA [J].
SANADA, M ;
MIYANO, T ;
IWADARE, S ;
WILLIAMSON, JM ;
ARISON, BH ;
SMITH, JL ;
DOUGLAS, AW ;
LIESCH, JM ;
INAMINE, E .
JOURNAL OF ANTIBIOTICS, 1986, 39 (02) :259-265
[7]   TOXIC FLUORINE COMPOUNDS CONTAINING THE C-F LINK .2. 2-FLUOROETHANOL AND ITS DERIVATIVES [J].
SAUNDERS, BC ;
STACEY, GJ ;
WILDING, IGE .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (APR) :773-777
[8]  
SCOLASTICO C, 1985, SYNTHESIS-STUTTGART, P850
[9]   ALPHA-ALKYLATION OF AMINO-ACIDS WITHOUT RACEMIZATION. PREPARATION OF EITHER (S)-ALPHA-METHYLDOPA OR (R)-ALPHA-METHYLDOPA FROM (S)-ALANINE [J].
SEEBACH, D ;
AEBI, JD ;
NAEF, R ;
WEBER, T .
HELVETICA CHIMICA ACTA, 1985, 68 (01) :144-154
[10]   ADDITION OF CHIRAL GLYCINE, METHIONINE, AND VINYLGLYCINE ENOLATE DERIVATIVES TO ALDEHYDES AND KETONES IN THE PREPARATION OF ENANTIOMERICALLY PURE ALPHA-AMINO-BETA-HYDROXY ACIDS [J].
SEEBACH, D ;
JUARISTI, E ;
MILLER, DD ;
SCHICKLI, C ;
WEBER, T .
HELVETICA CHIMICA ACTA, 1987, 70 (01) :237-261