A sequential electrochemical oxidation - Olefin metathesis strategy for the construction of bicyclic lactam based peptidomimetics

被引:31
作者
Beal, LM [1 ]
Moeller, KD [1 ]
机构
[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(98)00858-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A sequential electrochemical amide oxidation - ring closing olefin metathesis sequence has been used to overcome problems associated with the synthesis of seven-membered ring lactam containing bicyclic peptidomimetics. The synthesis of several previously unavailable bicyclic lactam building blocks for constructing constrained thyroliberin analogs is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4639 / 4642
页数:4
相关论文
共 18 条
[1]  
BLECHERT S, 1997, ANGEW CHEM INT EDIT, V36, P2036
[2]   Chirospecific syntheses of conformationally constrained 7-azabicycloheptane amino acids by transannular alkylation [J].
Campbell, JA ;
Rapoport, H .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6313-6325
[3]  
CHU W, UNPUB
[4]   STEREOSELECTIVE ADDITION OF GRIGNARD-DERIVED ORGANOCOPPER REAGENTS TO N-ACYLIMINIUM IONS - SYNTHESIS OF ENANTIOPURE 5-SUBSTITUTED AND 4,5-SUBSTITUTED PROLINATES [J].
COLLADO, I ;
EZQUERRA, J ;
PEDREGAL, C .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :5011-5015
[5]  
FOBIAN YM, 1996, THESIS WASHINGTON U
[6]  
FONT J, 1986, THESIS WASHINGTON U
[7]   RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].
GRUBBS, RH ;
MILLER, SJ ;
FU, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452
[8]  
HANAU CE, UNPUB
[9]  
Laakkonen L, 1996, MOL PHARMACOL, V49, P1092
[10]   Conformationally restricted TRH analogs: The compatibility of a 6,5-bicyclic lactam-based mimetic with binding to TRH-R [J].
Li, WH ;
Moeller, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (42) :10106-10112