The constituents of Schizandra chinensis Baill. IX. The cleavage of the methylenedioxyl moiety with lead tetraacetate in benzene, and the structure of angeloylgomisin Q.

Abstract

A procedure for selective cleavage of the methylenedioxyl moiety with lead tetraacetate in dry benzene is described. Piperonylic acid methyl ester (5), 4-nitro-1, 2-methylenedioxybenzene (6), 3, 4-methylenedioxytoluene (7), 2, 3-methylenedioxyanisole (8) and gomisin A (9) afforded protocatechuic acid (12), 4-nitrocatechol (13), 3, 4-dihydroxytoluene (14), 2, 3-dihydroxyanisole (15) and compound 16, respectively. The structure of angeloylgomisin Q isolated from the fruits of Schizandra chinensis BAILL. (Schizandraceae), was elucidated as 1 by using the above reaction.