Pigments of fungi. XLVII: Cardinalic acid, a new anthraquinone carboxylic acid from the New Zealand toadstool dermocybe cardinalis and the synthesis and x-ray crystal structure of methyl 1,7,8-tri-O-methylcardmalate

Abstract

Cardinalic acid (l,7,8-trihydroxy-6-methoxy-3-methyl-9,10-dioxoanthracene-2-carboxylic acid) (4) and the known anthraquinone carboxylic acids endocrocin (1), dermolutein (2) and cinnalutein (3) have been isolated from the New Zealand toadstool Dermocybe cardinalis. Methyl 1,7,8-tri-O-methylcardinalate (5) has been prepared both by permethylation of the natural product (4) and from 2,6-dichloro-l,4- benzoquinone by two consecutive regioselective Diels-Alder cycloaddition reactions. A single-crystal X-ray structure analysis of the ester (5) corroborates the structure of the natural product (4) and confirms the outcome of both cycloaddition reactions.