Senoxydene

In 1979, Bohlmann and Zdero reported the isolation and an unusual sesquiterpene hydrocarbon from Senecio oxyodontus This substance was formulated as 766 on the basis of its spectral characteristics and called senoxydene. However, Galemmo and Paquette have recently prepared this particular compound and determined that it is not identical to the natural product. Their pathway, which is summarized in Scheme LXXXVII, begins by transforming 4,4-dimethylcyclopentenone into bicyclic... 

A new tricyclic hydrocarbon, senoxydene, which has been isolated from Senecio oxyodontus, has been assigned the structure (304) on the basis of its n.m.r. spectrum together with that of the corresponding epoxide.It is suggested that once again humulene could act as the precursor (Scheme 48) see, however, p. 104. 

Although isocomene (668), mentioned above, is included in this section it is likely that this hydrocarbon, together with modhephene (679), is derived from a caryophyllene-type precursor. Indeed one can conceive of a biogenetic pathway (Scheme 87) which encompasses both these compounds as well as botrydial (681), quadrone (682), and the recently isolated senoxydene (304). " To lend partial credence to this scheme is the fact that the hydrocarbon (680) is a product of acid-catalysed rearrangement of isocaryophyllene (678). ... 

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