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A proposal for the mechanism-of-action of diazoparaquinone natural products.

ABSTRACT: Treatment of the representative diazoparaquinone prekinamycin dimethyl ether with Bu3SnH/AIBN in aromatic solvents furnishes moderate-to-good yields of formal aryl adducts wherein a molecule of solvent is attached to the carbon (C(11)) previously bearing the diazo function. Substituent studies provide evidence in support of a radical aromatic substitution mechanism, in which radical addition to the diazoparaquinone function generates an intermediate C(11) vinylic radical.

SUBMITTER: Feldman KS

PROVIDER: S-EPMC2789421 | biostudies-literature | 2005 Nov

REPOSITORIES: biostudies-literature

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A proposal for the mechanism-of-action of diazoparaquinone natural products.

Feldman Ken S KS Eastman Kyle J KJ

Journal of the American Chemical Society 20051101 44

Treatment of the representative diazoparaquinone prekinamycin dimethyl ether with Bu3SnH/AIBN in aromatic solvents furnishes moderate-to-good yields of formal aryl adducts wherein a molecule of solvent is attached to the carbon (C(11)) previously bearing the diazo function. Substituent studies provide evidence in support of a radical aromatic substitution mechanism, in which radical addition to the diazoparaquinone function generates an intermediate C(11) vinylic radical. ...[more]

PMID: 16262378

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