Journal of Organic Chemistry p. 3149 - 3155 (1980)
Update date:2022-08-04
Topics:
Rastetter, William H.
Nummy, Larry J.
Three isomeric amine-substituted arene oxides have been synthesized to serve as models for the postulated involvement of amino acid derived arene oxides during the biosyntheses of various epidithiadiketopiperazines.No biogenetic-type reactivity was noted for the arene oxides.In all three cases aromatization rather than amine/epoxide cyclization was observed.The failure to duplicate the presumed in vivo reactivity of aminoarene oxides is discussed in terms of possible enzyme-mediated cyclizations in the natural systems.
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