Organic & Biomolecular Chemistry
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.
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.