Towards a versatile synthesis of kainoids .1. Introduction of the C-3 and C-4 substituents

被引:33
作者
Baldwin, JE [1 ]
Bamford, SJ [1 ]
Fryer, AM [1 ]
Rudolph, MPW [1 ]
Wood, ME [1 ]
机构
[1] UNIV EXETER,DEPT CHEM,EXETER EX4 4QD,DEVON,ENGLAND
关键词
D O I
10.1016/S0040-4020(97)00190-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:5233 / 5254
页数:22
相关论文
共 26 条
[1]   A CONCISE APPROACH TO KAINOID ANALOGS [J].
BALDWIN, JE ;
RUDOLPH, M .
TETRAHEDRON LETTERS, 1994, 35 (33) :6163-6166
[2]  
BALDWIN JE, 1995, TETRAHEDRON LETT, V36, P4869
[3]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[4]   FACILE SYNTHESIS OF TERT-BUTYL ESTER OF N-PROTECTED AMINO-ACIDS WITH TERT-BUTYL BROMIDE [J].
CHEVALLET, P ;
GARROUSTE, P ;
MALAWSKA, B ;
MARTINEZ, J .
TETRAHEDRON LETTERS, 1993, 34 (46) :7409-7412
[5]  
Derome A.E., 1987, MODERN NMR TECHNIQUE
[6]  
DORMOY JR, 1986, SYNTHESIS-STUTTGART, P81
[7]  
FARINA V, 1991, SYNLETT, P157
[8]   PALLADIUM CATALYSIS IN CEPHALOSPORIN CHEMISTRY - GENERAL METHODOLOGY FOR THE SYNTHESIS OF CEPHEM SIDE-CHAINS [J].
FARINA, V ;
BAKER, SR ;
BENIGNI, DA ;
HAUCK, SI ;
SAPINO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5833-5847
[9]   SYNTHESIS OF NEW ACROMELIC ACID CONGENERS - NOVEL NEUROEXCITATORY AMINO-ACIDS ACTING ON GLUTAMATE RECEPTOR [J].
HASHIMOTO, K ;
SHIRAHAMA, H .
TETRAHEDRON LETTERS, 1991, 32 (23) :2625-2628
[10]  
HENDRICK.JB, 1973, TETRAHEDRON LETT, P4607