A facile synthesis of cephem side chains by palladium catalyzed cross-coupling of 3-substituted-Δ3-cephems with dialkylzinc or vinyltributyltin

被引:6
作者
Contento, M
Da Col, M
Galletti, P
Sandri, S
Umani-Ronchi, A
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2] Biochim OPOS SpA, I-20041 Agrate Brianza, MI, Italy
关键词
D O I
10.1016/S0040-4039(98)01940-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of 3-vinyl- and 3-alkyl-Delta(3)-cephems was performed in a regioselective manner by palladium acetate catalyzed reaction of 3-sulfonato- or 3-bromo-Delta(3)-cephems with dialkylzinc or vinyltributyltin. A new access to 3-alkyl-Delta(3)-cephems is opened, starting from the allenyl compound 10. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8743 / 8746
页数:4
相关论文
共 11 条
[1]  
CAINELLI G, 1994, SYNLETT, P243
[2]  
CURTIS NAC, 1980, RECENT ADV CHEM BETA, P203
[3]   A GENERAL-ROUTE TO 3-FUNCTIONALIZED 3-NORCEPHALOSPORINS [J].
FARINA, V ;
BAKER, SR ;
HAUCK, SI .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20) :4962-4966
[4]  
HETTRICK CM, 1991, J ORG CHEM, V53, P1489
[5]   CHEMISTRY OF CEPHALOSPORIN ANTIBIOTICS .19. TRANSFORMATION OF DELTA2-CEPHEM TO DELTA3-CEPHEM BY OXIDATION-REDUCTION AT SULFUR [J].
KAISER, GV ;
COOPER, RDG ;
KOEHLER, RE ;
MURPHY, CF ;
WEBBER, JA ;
WRIGHT, IG ;
VANHEYNI.EM .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (07) :2430-&
[6]   A NOVEL-APPROACH TO CEPHALOSPORINS FROM ALLENYLAZETIDINONES - A NEW CYCLIZATION STRATEGY VIA TANDEM CUPRATE ADDITION-SULFENYLATION [J].
KANT, J ;
ROTH, JA ;
FULLER, CE ;
WALKER, DG ;
BENIGNI, DA ;
FARINA, V .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4956-4966
[7]   A STEREOCONTROLLED SYNTHESIS OF CEFPROZIL AND RELATED CEPHEMS VIA ALLENYLAZETIDINONES .2. [J].
KANT, J ;
FARINA, V .
TETRAHEDRON LETTERS, 1992, 33 (25) :3563-3566
[8]   NUCLEOPHILIC-SUBSTITUTION OF 3-FLUOROSULFONYLOXY CEPHALOSPORINS WITH ORGANOCUPRATES [J].
ROTH, GP ;
PETERSON, SA ;
KANT, J .
TETRAHEDRON LETTERS, 1993, 34 (45) :7229-7230
[9]  
Sammes P. G, 1980, TOPICS ANTIBIOTIC CH, V4
[10]   Synthesis of 3-alkenyl-Delta(2)-cephems by copper(I) chloride-promoted alkenylation of 3-trifluoromethylsulfonyloxy-Delta 3-cephem with alkenyltributyltins [J].
Tanaka, H ;
Sumida, S ;
Torii, S .
TETRAHEDRON LETTERS, 1996, 37 (33) :5967-5970