Document Type

Article

Publication Date

11-2011

Source Publication

Organic & 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.

Comments

Accepted version. Organic & Biomolecular Chemistry, Vol. 9, No. 22 (November 2011): 7742-7747. DOI: © Royal Society of Chemistry 2011. Used with permission.

The spectral data used in the research for this article may be found here.

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