title: Reactivity of acyclic (pentadienyl)iron(1+) cations: synthetic studies directed toward the frondosins.
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.
authors.affiliation: Department of Chemistry, Marquette University, Milwaukee, WI, USA.
authors.forename: Do W
authors.initials: DW
authors.lastname: Lee
authors.forename: Rajesh K
authors.initials: RK
authors.lastname: Pandey
authors.forename: Sergey
authors.initials: S
authors.lastname: Lindeman
authors.forename: William A
authors.initials: WA
authors.lastname: Donaldson
mesh_terms: D000466:Alkadienes / Q000737:chemistry; D000818:Animals; D059001:Aquatic Organisms / Q000737:chemistry; D001327:Autoimmune Diseases / Q000188:drug therapy; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D002412:Cations / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D005290:Ferric Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D016209:Interleukin-8 / Q000037:antagonists & inhibitors / Q000276:immunology; D007501:Iron / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009369:Neoplasms / Q000188:drug therapy / Q000276:immunology; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry; D053700:Receptors, Interleukin-8 / Q000037:antagonists & inhibitors / Q000276:immunology
chemical_list: D000466:Alkadienes; D001643:Bridged Bicyclo Compounds; D002412:Cations; D005290:Ferric Compounds; D016209:Interleukin-8; D053700:Receptors, Interleukin-8; C524890:frondosin A; D007501:Iron