A diastereoselective synthesis of the tetrahydropyridazinone core of 2-oxo-1,6-diazobicyclo[4.3.0]nonane-9-carboxylate-based peptidomimetics starting from (S)-phenylalanine

被引:20
作者
Gardiner, J [1 ]
Abell, AD [1 ]
机构
[1] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand
关键词
D O I
10.1016/S0040-4039(03)00882-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A diastereoseletvive synthesis of a peptidic tetrahydropyridazinone 10 from (S)-phenylalanine is reported. This derivative was then converted to the bicyclic peptidomimetic 11, an important class of beta-strand mimetic. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4227 / 4230
页数:4
相关论文
共 12 条
[1]   Synthesis and x-ray structure of a 1,2,3,6-tetrahydropyridine-based phenylalanine mimetic [J].
Abell, AD ;
Gardiner, J ;
Phillips, AJ ;
Robinson, WT .
TETRAHEDRON LETTERS, 1998, 39 (51) :9563-9566
[2]   Chemistry and X-ray crystallographic structure of N-protected (5-oxo-1,3-oxazolidin-4-yl)acetic acids: Versatile intermediates in the synthesis of peptidomimetics [J].
Abell, AD ;
Edwards, RA ;
Oldham, MD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1655-1662
[3]  
ABELLA D, 1996, J CHEM SOC P1, P1299
[4]   THE DESIGN AND SYNTHESIS OF THE ANGIOTENSIN CONVERTING-ENZYME-INHIBITOR CILAZAPRIL AND RELATED BICYCLIC COMPOUNDS [J].
ATTWOOD, MR ;
HASSALL, CH ;
KROHN, A ;
LAWTON, G ;
REDSHAW, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06) :1011-1019
[5]   Secondary structure peptide mimetics:: Design, synthesis, and evaluation of β-strand mimetic thrombin inhibitors [J].
Boatman, PD ;
Ogbu, CO ;
Eguchi, M ;
Kim, HO ;
Nakanishi, H ;
Cao, BL ;
Shea, JP ;
Kahn, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (08) :1367-1375
[6]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[7]  
Fuchi N, 2002, SYNLETT, P285
[8]   The synthesis of β-strand mimetic templates via regioselective 1,3-dipolar cycloaddition with vinylsulfone [J].
Fuchi, N ;
Doi, T ;
Harada, T ;
Urban, J ;
Cao, BL ;
Kahn, M ;
Takahashi, T .
TETRAHEDRON LETTERS, 2001, 42 (07) :1305-1308
[9]   Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics [J].
Hanessian, S ;
McNaughtonSmith, G ;
Lombart, HG ;
Lubell, WD .
TETRAHEDRON, 1997, 53 (38) :12789-12854
[10]   Self-regeneration of stereocenters (SRS) - Applications, limitations, and abandonment of a synthetic principle [J].
Seebach, D ;
Sting, AR ;
Hoffmann, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2708-2748