Title

Preparation of Cyclohexenones from Acyclic (Pentadienyl)iron(1+) Cations: Synthetic Studies Directed toward the A-Ring of Dihydrotachysterols

Document Type

Article

Publication Date

10-2014

Source Publication

European Journal of Organic Chemistry

Source ISSN

1434-193X

Abstract

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.

Comments

European Journal of Organic Chemistry, Vol. 2014, No. 30 (October 2014): 6787–6795. DOI.