Lignans of Western Red Cedar (Thujaplicata Donn). VIII. Plicatinaphthol

Abstract

The isolation and structure of a new lignan, 1,6-dihydroxy-2-(hydroxymethyl)-7-methoxy-4-(3′,4′-dihydroxy-5′-methoxyphenyl)-3-naphthoic acid lactone (plicatinaphthol, 2), in which the 4-aryltetrahydronaphthalene structure of plicatin (1) has been aromatized to a 4-arylnaphthol nucleus are described. Proof of structure of the parent compound and its tetramethyl, tetraacetyl, and tetraethyl derivatives is presented both by analytical and spectral techniques, in addition to the synthesis of the tetramethyl derivative starting from podophyllotoxin.