e-Publications@Marquette

Title

Spectral Data for "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 V. Lindeman, Marquette UniversityFollow
William A. Donaldson, Marquette UniversityFollow

Grant Title

Natural Products Synthesis via Organoiron Methodology

Document Type

Spectral Data

Format Type

.pdf

Publication Date

11-2012

Abstract

Spectral data created in the course of the research project. Supports specific findings in "Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins".

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.

Recommended Citation

Lee, Do W.; Pandey, Rajesh K.; Lindeman, Sergey V.; and Donaldson, William A., "Spectral Data for "Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins"" (2012). Natural Products Synthesis via Organoiron Methodology. 11.
https://epublications.marquette.edu/data_nps/11