Title: Thiazole and oxazole building blocks for combinatorial synthesis
Abstract: Three thiazole and oxazole containing amino acids were synthesized in good yields by condensation-cyclization. The active functional groups used, a C-terminal imino ester or a C-terminal aldehyde, reacted with both the amino groups and side chains of either serine or cysteine within 5 minutes at rt to form oxazolines or diasteriomeric mixtures of thiazolidines, respectively. The intermediate heterocyclic rings were then dehydrogenated to form the more stable, fully aromatic, rings. Ready availability of N-protected thiazole and oxazole-containing building blocks facilitates the solid-phase synthesis of natural products such as microcin B17 and other peptide-derived natural products that contain 2,4-linked thiazole and oxazole rings.
Publication Year: 1999
Publication Date: 1999-11-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 24
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