The mould metabolite culmorin has been degraded in a stepwise manner to tetrahydroeucarvone and converted in a simple reaction sequence to enantiolongiborneol. These and related studies have shown that culmorin is 2,6,6,9-tetramethyltricyclo[5,4,01,7,02,9]undecane-8,11-diol (Ia). The configurations assigned to the hydroxy-groups are based on chemical evidence and confirmed by appropriate n.m.r. studies.
D. H. R. Barton and N. H. Werstiuk, J. Chem. Soc. C, 1968, 148 DOI: 10.1039/J39680000148
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