BIOMIMETIC SYNTHESIS OF 4-ACETYLBENZOXAZOLIN-2(3H)-ONE ISOLATED FROM ZEA-MAYS

4-Acetylbenzoxazolin-2(3H)-one has been prepared biomimetically during attempts to synthesize the hemiacetalic hydroxamic acid 5-acetyl-2,4- dihydroxy-2H-1,4-benzoxazin-3 (4H)-one by the immediate degradation of this unstable compound generated as an intermediate. Thus, 4-acetylbe nzoxazolin-2(3H)one recently isolated from Zea mays kernels, and simil ar to other benzoxazolin-2(3H)-ones known from plant sources, is assum ed to have originated from the degradation of natural 5-acetyl-2,4-dih ydroxy-2H-1,4-benzoxazin-3(4H)-one which in turn could have been enzym atically released by a beta-glucosidase from the corresponding 2-beta- D-glucoside.