METABOLITES OF BIRDS NEST FUNGI .4. ISOLATION AND STRUCTURE DETERMINATION OF CYBULLOL, A METABOLITE OF CYATHUS-BULLERI BRODIE

Cybullol, a metabolite of C. bulleri Brodie, was shown to be (2S,5S,6S,10S)-cis-6,trans-10-dimethyl-r-2-cis-5-decalindiol by a combination of chemical and physical methods. The mass spectra and the 1H and 13C PMR spectra of cybullol and derivatives are discussed. The absolute configuration of cybullol was deduced from the circular dichroism spectra of a ketol. Cybullol was transformed into the fungal metabolite (-)-geosmin. This correlation establishes the absolute configuration of (-)-geosmin.