The First Syntheses of the 1-Oxo-2-oxa-5-azaspiro[3.4]octane Ring System Found in Oxazolomycin

The First Syntheses of the 1-Oxo-2-oxa-5-azaspiro[3.4]octane Ring System Found in Oxazolomycin

l-Proline was utilized to prepare an optically active 1-oxo-2-oxa-5-azaspiro[3.4]octane for the first time. The synthesis of the racemic system, using a tandem aldol−lactonization reaction, is also described. Ruthenium tetroxide oxidation of these compounds afforded the corresponding spiro β-lactone...

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Veröffentlicht in:Organic letters 2000-07, Vol.2 (14), p.1987-1990
Hauptverfasser: Papillon, Julien P. N, Taylor, Richard J. K
Format: Artikel
Sprache:eng
Schlagworte:
Antiviral Agents - chemical synthesis
Crystallography, X-Ray
Lactones - chemical synthesis
Magnetic Resonance Spectroscopy
Molecular Conformation
Oxazoles - chemical synthesis
Oxidation-Reduction
Pyrrolidinones
Spiro Compounds - chemical synthesis
Stereoisomerism
Streptomyces - chemistry
Streptomyces - metabolism
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Zusammenfassung:l-Proline was utilized to prepare an optically active 1-oxo-2-oxa-5-azaspiro[3.4]octane for the first time. The synthesis of the racemic system, using a tandem aldol−lactonization reaction, is also described. Ruthenium tetroxide oxidation of these compounds afforded the corresponding spiro β-lactone γ-lactams.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0058792