New Synthesis of Megastigma-4,6,8-trien-3-ones, 3-Hydroxy-β-ionol, 3-Hydroxy-β-ionone, 5,6-Epoxy-3-hydroxy-β-ionol, and 3-Oxo-α-ionol

Article abstract of DOI:10.1246/bcsj.55.1907

The Lewis acid-catalyzed reaction of 1-trimethylsiloxy-1,3-cyclohexadienes with aldehydes and trialkyl orthoformates afforded the corresponding 4-substituted 2-cyclohexenones.A new reaction of 2,4,6-trienones with m-chloroperbenzoic acid followed by the reduction with zinc in acetic acid gave 7-hydroxy-3,5-dienones.Utilizing these efficient reactions, megastigma-4,6,8-trien-3-ones, 3-hydroxy-β-ionol, 3-hydroxy-β-ionone, 5,6-epoxy-3-hydroxy-β-ionol, and 3-oxo-α-ionol were successfully synthesized.