Neoclovene, a product from acid-catalysed rearrangement of caryophyllene, has been synthesised in such a manner as to demonstrate the probable intermediacy of a specific carbonium ion derived from (4S,7R)-3,3,7,11-tetramethyltricyclo[5,4,0,01,4]undecan-11-ol (24) in the formation of neoclovene from caryophyllene. This work also provides additional support for the relative configuration assigned to neoclovene.
T. F. W. McKillop, J. Martin, W. Parker, J. S. Roberts and J. R. Stevenson, J. Chem. Soc. C, 1971, 3375 DOI: 10.1039/J39710003375
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