Total synthesis of sequential retro-peptide oligomers

被引：8

作者：

Ceretti, S

Luppi, G

De Pol, S

Formaggio, F

Crisma, M

Toniolo, C

Tomasini, C ^{[1
]}

机构：

[1] Univ Bologna, Alma Mat Studiorum, Dept Chem G Ciamician, I-40126 Bologna, Italy

[2] Univ Padua, Dept Chem, CNR, Inst Mol Chem, I-35131 Padua, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 20期

关键词：

conformation analysis; Curtius rearrangement; peptidomimetics; retro-peptides;

D O I：

10.1002/ejoc.200400242

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of sequential oligomers of retro-peptides of the general formula Boc(-gGly-mAib)(n)-OBn, starting from dimethylmalonic acid, has been carried out in good overall yield. The key step is the formation of the gGly unit >N-CH2-N<, which is easily obtained in a one-pot/threestep reaction from BnO-mAib-Gly-OH and diphenylphosphoryl azide. The synthesis of the sequential oligomers of RCO(-gAla-mAib)(n)-OR' was also attempted, but the oligomerization step failed because the gAla moiety readily decomposes or racemizes. (C) Wiley-VCH Verlag GmbH Co.

引用

页码：4188 / 4196

页数：9

共 37 条

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