Design of a Cyclopropyl Quinone Methide

CHARACTERIZING QUINONE METHIDES BY SPECTRAL GLOBAL FITTING 

SCHEME 7.14 Cyclopropyl quinone methide formation upon reductive activation. The CC-1065 A-ring is shown in the inset. 

FIGURE 7.13 Molecular model of the pyrrolo [ 1,2- 2] i ndol e showing the site of nucleophile attack that provides a favorable stereoelectronic effect. The inset shows expected orbital interactions. 

SCHEME 7.16 Reductive alkylation of the alternating DNA polymer, poly d(GC), at the guanine N(7) position followed by elimination to afford the alkene. 

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Ouyang, A. Skibo, E. B. Design of a cyclopropyl quinone methide reductive alkylating agent. J. Org. Chem. 1998, 63, 1893-1900. 

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