Polyprenyl derivatives from the sponge Ircinia spinosula

Unsubstituted prenylated benzoquinones, a novel group of terpenoid quinones, the corresponding quinols, together with the hydroxylated 2-octaprenyl-quinol (VII) have been identified in the marine sponge Ircinia spinosula. From the same sponge we have also isolated the prenylated furan derivatives XI, XII and XIII, named furospinosulin-1, -2 and -3, and an unusual C-31 difuranoterpene, difurospinosulin (XIV). The synthesis of 2-heptaprenyl-1,4-benzoquinol (V) is reported.