19912-67-5Relevant articles and documents
Total Synthesis of (+/-)-Epicubenol
Cane, David E.,Tandon, Manish
, p. 5351 - 5354 (1994)
The sesquiterpenoid microbial metabolite (+/-)-epicubenol (1) has been synthesized in 8 steps from readily available diene aldehyde (7) using an intramolecular Diels-Alder reaction.
Thermal Rearrangement of Bicyclogermacrane-1,8-dione. Synthesis of Humulenedione and (-)-Cubenol, Starting from Natural (+)-Aromadendrene - V
Gijsen, Harrie J. M.,Wijnberg, Joannes B. P. A.,Groot, Aede de
, p. 4745 - 4754 (1994)
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 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 hydrogen shift, humulane, cadinane
Epicubebol and Related Sesquiterpenoids from the Brown Alga Dictyopteris divaricata
Suzuki, Minoru,Kowata, Nobuhiko,Kurosawa, Etsuro
, p. 2366 - 2368 (2007/10/02)
Epicubebol has been isolated from the methanol extracts of the brown alga Dictyopteris divaricata as the major constituent.Cadinane-type sesquiterpenes, cubebenes, δ-cadinene, cubenol, and epicubenol, as well as two sesquiterpene methyl ethers as minor constituents have also been obtained from the extracts.