Studies on Active Principles of Tars. X. The Structures and Some Reactions of Antifungal Constituents in Pix Pini

Abstract

By following the antifungal activity, four antifungal principles, acetovanillone(1), two new cyclic β-diketones, (2 and 3), and an unknown compound (4), were isolated from wood tar, Pix Pini, which has been used traditionally for the treatment of fungal diseases in Japan. The structures of 2 and 3 were established by synthesis to be 1, 1', 3, 3'-tetraoxo-2, 2'-bicyclopentyl and its 4-methyl derivative, respectively. Chemical reactivities and physical properties of 2 and 3 are also described.