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Reactivity of (3-Methylpentadienyl)iron(1+) Cation: Late-stage Introduction of a (3-Methyl-2Z,4-pentadien-1-yl) Side Chain

Subhabrata Chaudhury, Shukun Li, William A. Donaldson


The 3-methyl-2Z,4-pentadien-1-yl sidechain is found in various sesquiterpenes and diterpenes. A route for the late stage introduction of this functionality was developed which relies on nucleophilic attack on the (3-methylpentadienyl)iron(1+) cation, followed by oxidative decomplexation.  This methodology was applied to the synthesis of the proposed structure of heteroscyphic acid A methyl ester.  Realization of this synthesis led to a correction of the proposed structure.

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