Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone derivatives

被引:21
作者
Kanno, O [1 ]
Miyauchi, M [1 ]
Kawamoto, I [1 ]
机构
[1] Sankyo Co Ltd, Med Chem Res Labs, Shinagawa Ku, Tokyo 1408710, Japan
关键词
D O I
10.3987/COM-99-8689
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((S)-2) and (R)-4-acetylthio-2-pyrrolidinone (5), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)-3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide (14).
引用
收藏
页码:173 / 181
页数:9
相关论文
共 11 条
[1]  
BANFI S, 1984, FARMACO-ED SCI, V39, P16
[2]   A PRACTICAL ASYMMETRIC-SYNTHESIS OF CARNITINE [J].
KITAMURA, M ;
OHKUMA, T ;
TAKAYA, H ;
NOYORI, R .
TETRAHEDRON LETTERS, 1988, 29 (13) :1555-1556
[3]  
Kobayashi S, 1999, SYNLETT, P909
[4]   A novel oral carbapenem CS-834: Chemical stability of pivaloyloxymethyl esters of carbapenems and cephalosporins in phosphate buffer solution [J].
Miyauchi, M ;
Kanno, O ;
Kawamoto, I .
JOURNAL OF ANTIBIOTICS, 1997, 50 (09) :794-796
[5]   Synthesis and structure-activity relationships of a novel oral carbapenem, CS-834 [J].
Miyauchi, M ;
Endo, R ;
Hisaoka, M ;
Yasuda, H ;
Kawamoto, I .
JOURNAL OF ANTIBIOTICS, 1997, 50 (05) :429-439
[6]  
PELLEGATA R, 1978, SYNTHESIS-STUTTGART, P614
[7]   SYNTHESIS OF ENANTIOMERICALLY PURE GAMMA-AMINO-BETA-HYDROXYBUTYRIC ACID USING MALIC-ACID AS THE CHIRAL PRECURSOR [J].
RAJASHEKHAR, B ;
KAISER, ET .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5480-5484
[8]  
SANTANIELLO E, 1984, J CHEM RES-S, P132
[9]  
Seki M, 1999, SYNTHESIS-STUTTGART, P745
[10]   SYNTHETIC CARBAPENEM ANTIBIOTICS .3. 1-METHYL THIENAMYCIN [J].
SHIH, DH ;
CAMA, L ;
CHRISTENSEN, BG .
TETRAHEDRON LETTERS, 1985, 26 (05) :587-590