METAL-PROMOTED THIYL RADICAL CYCLIZATIONS IN BETA-LACTAM ANTIBIOTICS

被引:20
作者
CABRI, W [1 ]
CANDIANI, I [1 ]
BEDESCHI, A [1 ]
SANTI, R [1 ]
机构
[1] IST G DONEGANI SPA MONTEDISON,I-28100 NOVARA,ITALY
关键词
THIOL; RADICAL CYCLIZATION; IRON; MANGANESE;
D O I
10.1016/S0040-4039(00)61285-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular thiyl radical addition to a double bond promoted by Fe(III) and Mn(III) is described. The stabilized radical intermediate afforded by subsequent hydrogen abstraction cephams 4 and 5.
引用
收藏
页码:4783 / 4786
页数:4
相关论文
共 11 条
[1]   ENZYMATIC CONVERSION OF DEUTERATED ANALOGS OF DELTA-L-ALPHA-AMINOADIPOYL-L-CYSTEINYL-D-ALLYLGLYCINE, AN UNNATURAL SUBSTRATE FOR ISOPENICILLIN N SYNTHASE - A UNIFIED THEORY OF 2ND RING-CLOSURE [J].
BALDWIN, JE ;
BRADLEY, M ;
TURNER, NJ ;
ADLINGTON, RM ;
PITT, AR ;
DEROME, AE .
TETRAHEDRON, 1991, 47 (38) :8223-8242
[2]   PENICILLIN BIOSYNTHESIS - STEREOCHEMISTRY OF DESATURATIVE AND HYDROXYLATIVE PATHWAYS FROM L-ALPHA-AMINOADIPOYL-L-CYSTEINYL-D-ISODEHYDROVALINE WITH ISOPENICILLIN-N SYNTHASE [J].
BALDWIN, JE ;
ADLINGTON, RM ;
KING, LG ;
PARISI, MF ;
SOBEY, WJ ;
SUTHERLAND, JD ;
TING, HH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (24) :1635-1637
[3]   THE BIOSYNTHESIS OF PENICILLINS AND CEPHALOSPORINS [J].
BALDWIN, JE ;
ABRAHAM, E .
NATURAL PRODUCT REPORTS, 1988, 5 (02) :129-145
[4]   THE RING EXPANSION OF PENAMS TO CEPHAMS - A POSSIBLE BIOMIMETIC PROCESS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
KANG, TW ;
LEE, E ;
SCHOFIELD, CJ .
TETRAHEDRON, 1988, 44 (18) :5953-5957
[5]   EVIDENCE FOR AN INSERTION HOMOLYSIS MECHANISM FOR CARBON SULFUR BOND FORMATION IN PENICILLIN BIOSYNTHESIS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
MARQUESS, DG ;
PITT, AR ;
RUSSELL, AT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (13) :856-858
[6]  
GORDON EM, 1977, TETRAHEDRON LETT, P3425
[7]  
MAKI Y, 1976, TETRAHEDRON LETT, P4291
[8]   OXIDATION OF THIOLS TO DISULFIDES WITH MANGANIC TRIS (ACETYLACETONATE) [J].
NAKAYA, T ;
ARABORI, H ;
IMOTO, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1970, 43 (06) :1888-+
[9]  
NARISADA M, 1978, TETRAHEDRON LETT, P1755
[10]  
Sheldon R.A., 1981, METAL CATALYZED OXID