TERPENOID CHEMISTRY .19. DEHYDRO-MYODESMONE AND DEHYDROISO-MYODESMONE, TOXIC FURANOID SESQUITERPENE KETONES FROM MYOPORUM-DESERTI
TERPENOID CHEMISTRY .19. DEHYDRO-MYODESMONE AND DEHYDROISO-MYODESMONE, TOXIC FURANOID SESQUITERPENE KETONES FROM MYOPORUM-DESERTI
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DOI：
10.1071/ch9721779
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发表时间：
1972-01-01
影响因子：
1.1
通讯作者：
SUTHERLAND, MD
中科院分区：
文献类型：
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作者：
BLACKBURNE, ID;SUTHERLAND, MD
另一种精油品种（西奥多品种）的Myoporum deserti A. Cunn。产生一种精油，其含有c.50%的混合物（1:1至2:1）的两种先前未描述的呋喃类倍半萜酮，即(-)-1' s,5'S-1-[2'-（β-呋喃基）-5'-甲基环戊烯-2'-烯基]-3-甲基丁-2-烯-1-酮(4),b.p。117º/1 mm, m.p 26-27º，[x]D -254º和(-)-5 - s -1-[2'-(β-furyl)-5'-乙基环戊烯-1 '-烯基]-3-甲基-2-en-1-one (3), b.p 118º/1 mm, [x]D -67º，是已知的Jackson品种的酮类的脱氢衍生物。(3)和(4)的结构由(3)和(4)的碱催化平衡、(4)的氢化反应和(3)的氧化反应得到(+)-2-甲基戊二酸证实。酮类对小鼠有毒，并且已经在生长在昆士兰州中部Theodore， Augathella， Tambo和Jackson附近的植物的M. deserti油中被发现。
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'-(β-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'-(β-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.