THE USE OF RADICAL DECARBOXYLATION IN THE PREPARATION OF 1-METHYLCARBAPENEM ANTIBIOTIC PRECURSORS FROM D-GLUCOSAMINE

被引：12

作者：

ANAYA, J

BARTON, DHR

CABALLERO, MC

GERO, SD

GRANDE, M

LASO, NM

HERNANDO, JIM

机构：

[1] TEXAS A&M UNIV,DEPT CHEM,COLLEGE STN,TX 77843

[2] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)86289-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereocontrolled synthesis of optically active 1-methylcarbapenams has been performed by radical cyclization and radical decarboxylation. 1,3,4-Trisubstituted-2-azetidinones, prepared by the Staudinger reaction with D-glucosamine as chiral auxiliary and sorbic acid were used as starting materials.

引用

收藏

页码：2137 / 2140

页数：4

相关论文

共 17 条

[1]

ADONIAS M, 1994, IN PRESS ACTA CRYS B

[2] STRUCTURE AND ABSOLUTE-CONFIGURATION OF THIENAMYCIN [J].

ALBERSSCHONBERG, G ;

ARISON, BH ;

HENSENS, OD ;

HIRSHFIELD, J ;

HOOGSTEEN, K ;

KACZKA, EA ;

RHODES, RE ;

KAHAN, JS ;

KAHAN, FM ;

RATCLIFFE, RW ;

WALTON, E ;

RUSWINKLE, LJ ;

MORIN, RB ;

CHRISTENSEN, BG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (20) :6491-6499

[3] THE USE OF RADICAL CYCLIZATION IN THE PREPARATION OF SUBSTITUTED METHYL CARBAPENEM ANTIBIOTIC PRECURSORS [J].

ANAYA, J ;

BARTON, DHR ;

GERO, SD ;

GRANDE, M ;

MARTIN, N ;

TACHDIJIAN, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (06) :867-869

[4]

ANAYA J, 1994, IN PRESS ACTA CRYS B

[5] NEW AND IMPROVED METHODS FOR THE RADICAL DECARBOXYLATION OF ACIDS [J].

BARTON, DHR ;

CRICH, D ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :939-941

[6] THE INVENTION OF RADICAL REACTIONS .25. A CONVENIENT METHOD FOR THE SYNTHESIS OF THE ACYL DERIVATIVES OF N-HYDROXYPYRIDINE-2-THIONE [J].

BARTON, DHR ;

SAMADI, M .

TETRAHEDRON, 1992, 48 (35) :7083-7090

[7] INVENTION OF NEW REACTIONS USEFUL IN THE CHEMISTRY OF NATURAL-PRODUCTS [J].

BARTON, DHR ;

ZARD, SZ .

PURE AND APPLIED CHEMISTRY, 1986, 58 (05) :675-684

[8]

BARTON DHR, 1990, J CHEM SOC P1, V11, P3211

[9] QUANTITATIVE DEALKYLATION OF ALKYL ESTERS VIA TREATMENT WITH TRIMETHYLSILYL IODIDE - NEW METHOD FOR ESTER HYDROLYSIS [J].

JUNG, ME ;

LYSTER, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (03) :968-969

[10]

KAHAN JS, 1979, J ANTIBIOT, V32, P1