Oxidation of colupulone (I) produces a complex mixture, separation of which by counter-current distribution gives the cyclopenta[b]furan (III) and the cyclopenta[b]pyran (IV). Support for these structures comes mainly from n.m.r. and mass spectral data.
R. Van den Bossche, M. Anteunis, M. Vandewalle and M. Verzele, J. Chem. Soc., Perkin Trans. 1, 1972, 1599 DOI: 10.1039/P19720001599
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