Metabolites of the higher fungi. Part 19. Serpenone, 3-methoxy-4-methyl-5-prop-1-enylfuran-2(5H)-one, a new γ-butyrolactone from the fungus Hypoxylon serpens(Barrons strain)(Persoon ex Fries)Kickx

Abstract

Culture solutions of the fungus Hypoxylon serpens(Barrons strain) contain a new butyrolactone as the major metabolite, which has been identified as 3-methoxy-4-methyl-5-prop-1-enylfuran-2(5H)-one (2), and small quantities of the reduced analogue, 3-methoxy-4-methyl-5-propylfuran-2(5H)-one (3); the structures have been established by synthesis of compound (3). A new rapid synthesis of the isomeric 4-methoxy-3,5-disubstituted analogues is described and the two groups of compounds are compared spectroscopically.