The Synthesis of Stypandrol, a Toxic Binaphthalenetetrol Isolated from Stypandra imbricata: New Syntheses of Dianellidin and Stypandrone

Abstract

New syntheses of the naphthalenoid natural products dianellidin [1-(1, 8-dihydroxy-3- methylnaphthalen-2-yl)ethanone] (2) and stypandrone [6-acetyl-5-hydroxy-7-methylnaphthalene- 1, 4-dione] (20), which rely on the Fries rearrangement, are described. This methodology is then applied to the synthesis of stypandrol [1, 1'-(1, 1', 8, 8'-tetrahydroxy-6, 6 '-dimethyl-2, 2 binaphthalene-7, 7'-diyl)bisethanone] (1), a toxic naphthalenetetrol isolated from Stypandra imbricata R.Br. (‘blind grass’). © 1988 ASEG.