Synthesis of peptidomimetics, δ- and ε-lactam tetrazoles

A concise two-step procedure for the synthesis of novel δ-lactam tetrazoles has been established via the Ugi-azide reaction using 5-oxohexanoic acid along with primary amines, isocyanides, and azidotrimethylsilane followed by 1,1'-carbonyldiimidazole-mediated intramolecular amide formation. Exp...

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Bibliographic Details
Published in:Molecular diversity 2012-08, Vol.16 (3), p.601-606
Main Authors: Gunawan, Steven, Keck, Kristen, Laetsch, Alex, Hulme, Christopher
Format: Article
Language:English
Subjects:
Chemistry Techniques, Synthetic
Diterpenes, Kaurane - chemistry
Lactams - chemistry
Peptidomimetics - chemical synthesis
Peptidomimetics - chemistry
Tetrazoles - chemical synthesis
Tetrazoles - chemistry
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Summary:A concise two-step procedure for the synthesis of novel δ-lactam tetrazoles has been established via the Ugi-azide reaction using 5-oxohexanoic acid along with primary amines, isocyanides, and azidotrimethylsilane followed by 1,1'-carbonyldiimidazole-mediated intramolecular amide formation. Expansion to ε-lactam tetrazole scaffolds was accomplished using methyl 6-oxoheptanoate via the same Ugi-azide reaction followed by basic hydrolysis and SOCl(2) activation to enable lactam formation.
ISSN:1573-501X
DOI:10.1007/s11030-012-9373-2