Faculty Collaboration Database

Reactivity of acyclic (pentadienyl)iron(1+) cations: synthetic studies directed toward the frondosins. Org Biomol Chem 2011 Oct 26;9(22):7742-7

Date

09/29/2011

Pubmed ID

21952606

DOI

10.1039/c1ob05720k

Scopus ID

2-s2.0-80054985302 (requires institutional sign-in at Scopus site)   6 Citations

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 CuCl(2), affords 6-aryl-3-methoxycarbonyl-1,4-cycloheptadienes via the presumed intermediacy of a cis-divinylcyclopropane.

Author List

Lee DW, Pandey RK, Lindeman S, Donaldson WA

Author

William Donaldson PhD Professor in the Department of Chemistry department at Marquette University

MESH terms used to index this publication - Major topics in bold

Alkadienes
Animals
Aquatic Organisms
Autoimmune Diseases
Bridged Bicyclo Compounds
Cations
Chemistry, Pharmaceutical
Ferric Compounds
Humans
Interleukin-8
Iron
Magnetic Resonance Spectroscopy
Models, Molecular
Neoplasms
Oxidation-Reduction
Porifera
Receptors, Interleukin-8