SECONDARY MOLD METABOLITES .34. ISOLATION AND STRUCTURE ELUCIDATION OF ILLUDOSIN, A NOVEL SESQUITERPENE FROM CLITOCYBE-ILLUDENS USING ONE AND 2-DIMENSIONAL NMR TECHNIQUES

The structure of illudosin 1, a novel sesquiterpene isolated from the still liquid cultures of Clitocybe illudens (= Omphalotus olearius), has been assigned on the basis of H-1 and C-13 NMR spectroscopic studies, inclduing H-1-C-13 heteronuclear correlation spectra (HETCOR and COLOC). The preferred conformation and the absolute configuration of the metabolite were deduced from NOE experiments and the application of the exciton chirality method on the dibenzoate 2. Illudosin may be regarded as an intermediate in the biosynthesis of the fomannosin 3.