Ethyl (R)-3-hydroxy-4-phenylthiobutyrate: Synthesis by the bakers' yeast reduction and use as a precursor of enantiomerically pure beta-lactam

被引:11
作者
Hayakawa, R [1 ]
Shimizu, M [1 ]
Fujisawa, T [1 ]
机构
[1] MIE UNIV,DEPT CHEM MAT,TSU,MIE 514,JAPAN
关键词
D O I
10.1016/0040-4039(96)01693-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bakers' yeast reduction of ethyl 3-oxo-4-phenylthiobutanoate gave ethyl (R)-3-hydroxy-4-phenylthiobutanoate with >99%ee. The resultant enantiomerically pure alcohol was easily transformed into beta-lactam without loss of its enatiomeric purity via the oxamate derivative. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:7533 / 7536
页数:4
相关论文
共 27 条
[21]   PENEMS, A NEW CLASS OF BETA-LACTAM ANTIBIOTICS .5. TOTAL SYNTHESIS OF RACEMIC "6-ALPHA-HYDROXYETHYLPENEMCARBOXYLIC ACIDS [J].
PFAENDLER, HR ;
GOSTELI, J ;
WOODWARD, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :2039-2043
[22]   A STEREOCONTROLLED SYNTHESIS OF (+)-THIENAMYCIN [J].
SALZMANN, TN ;
RATCLIFFE, RW ;
CHRISTENSEN, BG ;
BOUFFARD, FA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (19) :6161-6163
[23]  
SEEBACH D, 1986, SYNTHESIS-STUTTGART, P37
[24]   A NEW SYNTHETIC ROUTE TO THE KEY PRECURSOR OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS FROM (S)-METHYL 3-HYDROXY-2-METHYLPROPANOATE [J].
SHIRAI, F ;
NAKAI, T .
CHEMISTRY LETTERS, 1989, (03) :445-448
[25]   A NOVEL, DOUBLE-ASYMMETRIC ALDOL APPROACH TO THE SYNTHESIS OF A 1-BETA-METHYL CARBAPENEM ANTIBIOTIC PRECURSOR [J].
SHIRAI, F ;
NAKAI, T .
TETRAHEDRON LETTERS, 1988, 29 (49) :6461-6464
[26]   HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE REDUCTION OF 2-METHYL-3-OXOALKANOIC ACIDS BY USE OF FERMENTING BAKERS-YEAST [J].
WATABU, H ;
OHKUBO, M ;
MATSUBARA, H ;
SAKAI, T ;
TSUBOI, S ;
UTAKA, M .
CHEMISTRY LETTERS, 1989, (12) :2183-2184
[27]   SYNTHESIS AND X-RAY CRYSTAL-STRUCTURE DETERMINATION OF 1,3-BRIDGED BETA-LACTAMS - NOVEL, ANTI-BREDT BETA-LACTAMS [J].
WILLIAMS, RM ;
LEE, BH ;
MILLER, MM ;
ANDERSON, OP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1073-1081