THE SYNTHESIS OF 4-ACETOXY-AZETIDIN-2-ONES AS KEY INTERMEDIATES FOR BETA-LACTAMS

被引：28

作者：

KEHAGIA, K ^{[1
]}

UGI, IK ^{[1
]}

机构：

[1] TECH UNIV MUNICH,LEHRSTUHL ORGAN CHEM & BIOCHEM 1,D-85747 GARCHING,GERMANY

来源：

TETRAHEDRON | 1995年 / 51卷 / 35期

关键词：

D O I：

10.1016/0040-4020(95)00542-G

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthesis of a chiral precursor of a cephem derivative is described. Starting material is the inexpensive chiral-pool chemical aspartic acid. The central step in forming the beta-lactam moiety is an Ugi reaction.

引用

页码：9523 / 9530

页数：8

共 21 条

[1] BACKERS J, METHODEN ORG CHEM
[2] CIPERA JD, 1955, CHEM IND-LONDON, P16
[3] A SIMPLE 2-STEP SYNTHESIS OF DIPHENYLMETHYL ESTERS OF 2-OXO-1-AZETIDINEACETIC ACIDS
ISENRING, HP
HOFHEINZ, W
[J]. SYNTHESIS-STUTTGART, 1981, (05): : 385 - 387
[4] TOTAL SYNTHESIS OF (+/-)-THIENAMYCIN
JOHNSTON, DBR
SCHMITT, SM
BOUFFARD, FA
CHRISTENSEN, BG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) : 313 - 315
[5] MCMURRY JE, 1973, ORG SYNTH, V33, P70
[6] NEW SYNTHESIS OF 4-ACETOXY-2-AZETIDINONES BY USE OF ELECTROCHEMICAL OXIDATION
MORI, M
KAGECHIKA, K
SASAI, H
SHIBASAKI, M
[J]. TETRAHEDRON, 1991, 47 (4-5) : 531 - 540
[7] OBRECHT R, 1985, SYNTHESIS-STUTTGART, P400
[8] TOTAL SYNTHESIS OF THIENAMYCIN - A NEW APPROACH FROM ASPARTIC-ACID
REIDER, PJ
GRABOWSKI, EJJ
[J]. TETRAHEDRON LETTERS, 1982, 23 (22) : 2293 - 2296
[9] BENZYL ESTERS OF GLUTAMIC ACID
SACHS, H
BRAND, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (18) : 4610 - 4611
[10] SYNTHETIC STUDIES ON NOVEL BETA-LACTAM COMPOUNDS FROM L-ASPARTIC ACID
SATO, A
HIRATA, T
NAKAMIZO, N
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1983, 47 (04): : 799 - 806

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