Enantioselective synthesis of pseudotripeptides incorporating a γ-methylene derivative of 2,6-diaminopimelic acid:: Part 6

被引:13
|
作者
Balducci, D [1 ]
Porzi, G [1 ]
Sandri, S [1 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词
D O I
10.1016/j.tetasy.2004.02.005
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient enantioselective synthesis of pseudotripeptides 5, 8a-d and 13a and b incorporating a 2,6-diamino-4-methylene-1,7-heptandioic acid residue, has been accomplished starting from the glycine derived chiral synthon 1 (from L-valine). The absolute configuration of the new stereocentres was assigned on the basis of H-1 NMR spectra. The geometry of derivative 4 was deduced on the basis of H-1 NMR parameters (delta(NH) value, temperature coefficient, delta(NH) change upon addition of DMSO or CD3OD, NOE studies) and IR spectra. (C) 2004 Elsevier Ltd. All rights reserved.
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页码:1085 / 1093
页数:9
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