Title
Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins
Grant Title
Natural Products Synthesis via Organoiron Methodology
Document Type
Article
Publication Date
11-2011
Source Publication
Organic and 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.
Recommended Citation
Lee, Do W.; Pandey, Rajesh K.; Lindeman, Sergey V.; and Donaldson, William A., "Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins" (2011). Natural Products Synthesis via Organoiron Methodology. 3.
https://epublications.marquette.edu/data_nps/3
Document Rights and Citation of Original
Organic & Biomolecular Chemistry, Vol. 9, No. 22 (November 2011): 7742-7747. DOI: 10.1039/C1OB05720K.