TERPENE BIOSYNTHESIS .3. BIOSYNTHESIS OF (+)-CAMPHOR AND (-)-CAMPHOR IN ARTEMISIA, SALVIA, AND CHRYSANTHEMUM SPECIES
TERPENE BIOSYNTHESIS .3. BIOSYNTHESIS OF (+)-CAMPHOR AND (-)-CAMPHOR IN ARTEMISIA, SALVIA, AND CHRYSANTHEMUM SPECIES
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DOI：
10.1039/j39700002694
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发表时间：
1970-01-01
期刊：
影响因子：
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通讯作者：
BAXENDAL.D
中科院分区：
文献类型：
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作者：
BANTHROP.DV;BAXENDAL.D
(+)-樟脑和菊花合成的(-)-樟脑和(-)-樟脑在C-6原子上含有73-83%的示踪剂。剩余的碳原子在其他碳原子之间分布相当均匀。因此，异戊烯基焦磷酸酯是主要的放射性前体，并且，正如对相关物种生产的侧链衍生物所发现的那样，来自3，3-二甲基烯丙基焦磷酸酯的骨架部分没有被等量标记。这两个光学异构体的标记模式与各自的形式一致，它们都是通过将正中心加到双键上从α-松油醇的相应对映体形成的阳离子而得到的。排除了由α-松油醇的一种特殊对映体分别环合成C-2和C-6而形成樟脑的两种光学异构体的可能性。
(+)-Camphor biosynthesised from [2-14C]mevalonic acid by Artemisia californica or Salvia leucophylla L., and (–)-camphor similarly formed by Chrysanthemum balsamita L., contained 73–83% of the incorporated tracer at C-6 atom. The balance was fairly evenly distributed amongst the other carbon atoms. Isopentenyl pyrophosphate was thus the predominant radioactive precursor and, as was found for thujane derivatives produced by related species, that part of the skeleton derived from 3,3-dimethylallyl pyrophosphate was not equivalently labelled.The similarity of the labelling pattern for both optical isomers is consistent with each being formally derived from the cation formed from the corresponding enantiomer of α-terpineol by addition of the positive centre to the double bond. The formation of both optical isomers of camphor from a particular enantiomer of α-terpineol by cyclisation to C-2 and C-6, respectively, was ruled out.