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

Authors

Charles Felix Manful, Marquette University
William A. Donaldson, Marquette UniversityFollow

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

Accepted version. European Journal of Organic Chemistry, Vol. 2014, No. 30 (October 2014): 6787–6795. DOI. © 2014 Wiley-VCH Verlag. Used with permission.

Recommended Citation

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.
https://epublications.marquette.edu/chem_fac/349