
TY  - JOUR
A1  - Blackburne, ID 
A1  - Sutherland, MD 
T1  - Terpenoid chemistry. XIX. Dehydro- and Dehydroiso-myodesmone, toxic furanoid sesquiterpene ketones from <I>Myoporum deserti</I>
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1972
VL  - 25
IS  - 8
SP  - 1779
EP  - 1786
KW  - 
UR  - https://doi.org/10.1071/CH9721779 
N2  - A further essential-oil variety (the Theodore variety) of Myoporum deserti A. Cunn. yields an essential oil which contains c.50% of a mixture (1 : 1 to 2 : 1) of two previously undescribed furanoid sesquiterpene ketones which are (-)-1'S,5'S-1-[2'-(&#946;-furyl)-5'-methylcyclopent-2'-enyl]-3-methylbut-2-en-l-one (4),b.p. 117º/1 mm, m.p. 26-27º, [x]D -254º, and (-)-5'S-1-[2'-(&#946;-furyl)-5'-ethylcyclopent-l'-enyl]-3-methylbut-2-en-1-one (3), b.p. 118º/1 mm, [x]D -67º, and are dehydro derivatives of ketones known from the Jackson variety of M. desertz. The structures (3) and (4), deduced from spectral evidence, are confirmed by the base-catalysed equilibration of (3) and (4), the hydrogenation of (4) to dihydroisomyodesmone, and the oxidation of (3) to (+)-2-methylglutaric acid. The ketones are toxic to mice and have been recognized in M. deserti oils from plants growing in central Queensland in the vicinity of Theodore, Augathella, Tambo, and Jackson. 
ER  -

