Preparation of Cyclohexenones from Acyclic (Pentadienyl)iron(1+) Cations: Synthetic Studies Directed toward the A-Ring of Dihydrotachysterols
European Journal of Organic Chemistry
The reaction of tricarbonyl(3-methylpentadienyl)iron(1+) cation (7) with stabilized carbon nucleophiles affords 4-methyl-5-substituted cyclohexenones. Reaction of 7 with sodium bis[(+)-2-phenylcyclohexyl]malonate afforded a mixture of diastereomers (de = 60 %); the diastereomeric allylic alcohols resulting from Luche reduction of this mixture were separable by column chromatography. Issues in diastereoselectivity in approaches to synthons for the A-ring of the tachysterols from these cyclohexenones are reported.
Manful, Charles Felix and Donaldson, William A., "Preparation of Cyclohexenones from Acyclic (Pentadienyl)iron(1+) Cations: Synthetic Studies Directed toward the A-Ring of Dihydrotachysterols" (2014). Chemistry Faculty Research and Publications. 349.