The first syntheses of the 1-oxo-2-oxa-5-azaspiro[3.4]octane ring system found in oxazolomycin.
[reaction: see text] 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 beta-lactone gamma-lactams.
Papillon
J P
JP
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
Taylor
R J
RJ
D000998:Antiviral Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D007783:Lactones / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010080:Oxazoles / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D011760:Pyrrolidinones; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism
C413125:1-oxo-2-oxa-5-azaspiro(3.4)octane; D000998:Antiviral Agents; D007783:Lactones; D010080:Oxazoles; D011760:Pyrrolidinones; D013141:Spiro Compounds; C077919:diffusomycin