The first reported anionic oxy retro-ene reaction.
Treatment of the diol 6 with KH and 18-C-6 at room temperature gives the cyclopentenone 7 in good yields. Mechanistic analysis reveals that this is the first case of an anionic oxy retro-ene reaction followed by a tandem intramolecular aldol condensation. Reaction: see text.
Jung
M E
ME
Department of Chemistry and Biochemistry, University of California-Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095, USA. jung@chem.ucla.edu
Davidov
P
P
D000438:Alcohols / Q000737:chemistry; D000838:Anions; D002316:Cardiotonic Agents / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000138:chemical synthesis*; D008958:Models, Molecular; D010042:Ouabain / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000438:Alcohols; D000838:Anions; D002316:Cardiotonic Agents; D003517:Cyclopentanes; D010042:Ouabain; C013905:cyclopentenone