Synthesis of 5/7-, 5/8- and 5/9-bicyclic lactam templates as constraints for external β-turns

被引:26
作者
Duggan, HME [1 ]
Hitchcock, PB [1 ]
Young, DW [1 ]
机构
[1] Univ Sussex, Dept Chem, Brighton BN1 9QJ, E Sussex, England
关键词
D O I
10.1039/b503014e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 5/7-, 5/8- and 5/9-bicyclic lactams 3, 17, 5 and 6 have been synthesised as single diastereoisomers by a route involving ring closing olefin metathesis. The X-ray crystal structure of the amino acid hydrochloride 17 has been carried out and compared to that of the saturated external beta-turn constraint 18.
引用
收藏
页码:2287 / 2295
页数:9
相关论文
共 23 条
[1]   The synthesis of pyrimidin-4-yl substituted α-amino acids.: A versatile approach from alkynyl ketones [J].
Adlington, RM ;
Baldwin, JE ;
Catterick, D ;
Pritchard, GJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :855-866
[2]   L-VINYLGLYCINE [J].
AFZALIARDAKANI, A ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (24) :4817-4820
[3]   Stereospecific synthesis of (2S,4R)-[5,5,5-H-2(3)]leucine [J].
August, RA ;
Khan, JA ;
Moody, CM ;
Young, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (06) :507-514
[4]   BETA-TURN TOPOGRAPHY [J].
BALL, JB ;
HUGHES, RA ;
ALEWOOD, PF ;
ANDREWS, PR .
TETRAHEDRON, 1993, 49 (17) :3467-3478
[5]   Anodic amide oxidation/olefin metathesis strategies: Developing a unified approach to the synthesis of bicyclic lactam peptidomimetics [J].
Beal, LM ;
Liu, B ;
Chu, WH ;
Moeller, KD .
TETRAHEDRON, 2000, 56 (52) :10113-10125
[6]   Potent integrin antagonists from a small library of RGD-including cyclic pseudopeptides [J].
Belvisi, L ;
Bernardi, A ;
Checchia, A ;
Manzoni, L ;
Potenza, D ;
Scolastico, C ;
Castorina, M ;
Cupelli, A ;
Giannini, G ;
Carminati, P ;
Pisano, C .
ORGANIC LETTERS, 2001, 3 (07) :1001-1004
[7]  
Chiesa MV, 1996, SYNLETT, P441
[8]   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
[9]   Synthesis of an external beta-turn based on the GLDV motif of cell adhesion proteins [J].
Davies, DE ;
Doyle, PM ;
Hill, RD ;
Young, DW .
TETRAHEDRON, 2005, 61 (01) :301-312
[10]   Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins [J].
Davies, DE ;
Doyle, PM ;
Farrant, RD ;
Hill, RD ;
Hitchcock, PB ;
Sanderson, PN ;
Young, DW .
TETRAHEDRON LETTERS, 2003, 44 (49) :8887-8891