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The labelling pattern in the sesquiterpenoid culmorin biosynthesised from [2(S)-2-3H,2-14C]- and [5(R)-5-3H,2-14C]-mevalonate shows that the endo-C-10 proton originates from the 2(S) position whilst the C-11 hydroxy-group has displaced a pro-5(R) proton; in contrast to dendrobine an eleven-membered ring is implicated, and a pro-5(S)-mevalonoid proton migrates at an early stage in the biosynthesis.
J. R. Hanson and R. Nyfeler, J. Chem. Soc., Chem. Commun., 1975, 824 DOI: 10.1039/C39750000824
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