Biogenesis of Epidithiadiketopiperazines. Synthesis of Three Isomeric (β-Aminoethyl)benzene Oxides

Article abstract of DOI:10.1021/jo01304a002

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.