Michael McCrane - Trapping a Labile Adduct Formed Between an ortho-Quinone Methide and 2'-Deoxycytidine

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  Publication Details (including relevant citation   information):

  Organic Letters, 2011, 13,   1186-1189


  Selective oxidation by bis[(trifluoroacetoxy)iodo]benzene (BTI)   provides an effective trap for quenching adducts formed   reversibly between dC and an ortho-quinone methide (QM)   under physiological conditions.  A model adduct generated by   4-methyl-o-QM and 2'-deoxycytidine is rapidly converted   by intramolecular cyclization and loss of aromaticity to a   characteristic product for quantifying QM alkylation.    However, BTI induces a surprising rearrangement driven by   overoxidation of a derivative lacking an alkyl substituent at the   4-position of the QM.

  Address (URL): http://dx.doi.org/10.1021/ol200071p