Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins

Authors

Do W. Lee, Marquette UniversityFollow
Rajesh K. Pandey, Marquette University
Sergey Lindeman, Marquette UniversityFollow
William Donaldson, Marquette UniversityFollow

Document Type

Article

Publication Date

11-2011

Source Publication

Organic & Biomolecular Chemistry

Source ISSN

1477-0520

Abstract

A short, 4-step route to the scaffold of frondosin A and B is reported. The [1-methoxycarbonyl-5-(2′,5′-dimethoxyphenyl)pentadienyl]Fe(CO)₃⁺ cation was prepared in two steps from (methyl 6-oxo-2,4-hexadienoate)Fe(CO)₃. Reaction of this cation with isopropenyl Grignard or cyclohexenyllithium reagents affords (2-alkenyl-5-aryl-1-methoxycarbonyl-3-pentene-1,5-diyl)Fe(CO)₃ along with other addition products. Oxidative decomplexation of these (pentenediyl)iron complexes, utilizing CuCl₂, affords 6-aryl-3-methoxycarbonyl-1,4-cycloheptadienes via the presumed intermediacy of a cis-divinylcyclopropane.

Comments

Accepted version. Organic & Biomolecular Chemistry, Vol. 9, No. 22 (November 2011): 7742-7747. DOI: © 2011 Royal Society of Chemistry. Used with permission.

The spectral data used in the research for this article may be found here.

Recommended Citation

Lee, Do W.; Pandey, Rajesh K.; Lindeman, Sergey; and Donaldson, William, "Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins" (2011). Chemistry Faculty Research and Publications. 197.
https://epublications.marquette.edu/chem_fac/197