The antifungal factors in barley. IV. Isolation, structure, and synthesis of the hordatines

Careful fractionation of extracts prepared from barley coleoptiles gave small amounts of pure hordatines A and B and substantial amounts of a mixture of their glucosides. The structures of the hordatines were deduced by degradative and spectroscopic studies and by the synthesis of some degradation products. A synthesis of racemic hordatine A analogous to its probable biogenesis was achieved by the oxidative coupling of coumaroylagmatine.The possible role of the hordatines in lignification is briefly discussed.