Biosynthesis of C11 and C16 homoterpenes in higher plants;: Stereochemistry of the C-C-bond cleavage reaction
Biosynthesis of C11 and C16 homoterpenes in higher plants;: Stereochemistry of the C-C-bond cleavage reaction
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DOI：
10.1016/s0040-4020(98)00902-8
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发表时间：
1998-12-03
期刊：
影响因子：
2.1
通讯作者：
Feng, ZF
中科院分区：
文献类型：
--
作者：
Boland, W;Gäbler, A;Feng, ZF
在高等植物中，C-11同萜4，8-二甲基壬-1，3，7-三烯（1）来源于橙花叔醇（3）或香叶基丙酮（4）的氧化降解。键断裂的过渡态的几何形状已被证明是顺-周面的，对于3和4，通过将手性标记的氘代前体应用于Magnolia liliiflora nigra的花或利马豆Phaseolus lunatus的叶。描述了由去甲法呢烯（5）通过对映体环氧化物（2S，3R）-6和ent-6合成氘代手性代谢探针3和8。(C)1998爱思唯尔科技有限公司。保留所有权利。
In higher plants the C-11 homoterpene 4,8-dimethylnona-1,3,7-triene (1) originates from oxidative degradation of nerolidol (3) or geranylacetone (4). The geometry of the transition state of bond cleavage has been shown to be syn-periplanar, for both 3 and 4 by application of chirally labelled, deuterated precursors to flowers of Magnolia liliiflora nigra or leaves of the Lima bean Phaseolus lunatus. The synthesis of the deuterated, chiral metabolic probes 3 and 8 from nor-farnesene (5), via the enantiomeric epoxides (2S,3R)-6 and ent-6, is described. (C) 1998 Elsevier Science Ltd. All rights reserved.