[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.

This study demonstrates the first successful synthesis of the 1-oxo-2-oxa-5-azaspiro[3.4]octane ring system found in oxazolomycin using L-proline and a tandem aldol-lactonization reaction.

Paper

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

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