The first syntheses of the 1-oxo-2-oxa-5-azaspiro[3.4]octane ring system found in oxazolomycin

Authors
Papillon, JPB Taylor, RJK
Citation
Jpb. Papillon et Rjk. Taylor, The first syntheses of the 1-oxo-2-oxa-5-azaspiro[3.4]octane ring system found in oxazolomycin, ORG LETT, 2(14), 2000, pp. 1987-1990
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
14
Year of publication
2000
Pages
1987 - 1990
Database
ISI
SICI code
1523-7060(20000713)2:14<1987:TFSOT1>2.0.ZU;2-B
Abstract
GRAPHICS L-Proline was utilized to prepare an optically active 1-oxo-2-oxa-5-azaspir o[3.4]octane for the first time. The synthesis of the racemic system, using a tandem aldol-lactonization reaction, is also described. Ruthenium tetrox ide oxidation of these compounds afforded the corresponding spiro beta-lact one gamma-lactams.