
TY  - JOUR
A1  - Blackburne, ID 
A1  - Park, RJ 
A1  - Sutherland, MD 
T1  - Terpenoid chemistry.  XX. Myoporone and dehydromyoporone, toxic furanoid ketones from <I>Myoporum</I> and <I>Eremophila</I> species
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1972
VL  - 25
IS  - 8
SP  - 1787
EP  - 1796
KW  - 
UR  - https://doi.org/10.1071/CH9721787 
N2  - Certain samples of essential oils from Myoporum deserti, M. betcheanum, M. acuminatum, Eremophila maculata, and E. latrobei have been shown to contain myoporone and/or 10,ll-dehydromyoporone. The ambiguity regarding the stereochemistry of myoporone (previously known from M, bontioides) has been resolved,(-)-myoporone being shown to possess the S configuration by degradation to (S)-(+)-2-methylglutaric acid. (-)-Dehydromyoporone, m.p. 32.5-33.5, [x]D ? 15º, has the S configuration as shown by degradation to (S)-(-)-3-methyladipic acid and hydrogenation to (S)-(-)-myoporone, m.p. 17.5-19º, [x]D-5.3º. Both ketones activate the typical ngaione pathology on intraperitoneal injection into mice but myoporone is not toxic to sheep. Myoporone from Myoporum species shows wide variations in optical purity. 
ER  -

