Tetrahedron p. 4745 - 4754 (1994)
Update date:2022-08-16
Topics:
Gijsen, Harrie J. M.
Wijnberg, Joannes B. P. A.
Groot, Aede de
Treatment of a distillation tail of Eucalyptus globulus, containing mainly (+)-aromadendrene (1) and (-)-alloaromadendrene (2), with K/Al2O3 gives a quantitative conversion of 1 and 2 into isoledene (4).Oxidative cleavage of the central double bond in 4 produces (+)-bicyclogermacrane-1,8-dione (5).Thermal rearrangement of 5 gives via a homo <1,5> hydrogen shift at relatively low temperature the humulenedione 6, and at high temperature (FVP) the products 9 and 10 both with a cadinane skeleton.The naturally occurring humulenedione (7) and (-)-cubenol (17) can be synthesized starting from 6 and 9, respectively. - Key Words: sesquiterpene, flash vacuum pyrolysis, homo <1,5> hydrogen shift, humulane, cadinane
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