A chemoenzymatic synthesis of the linear triquinane (-)-hirsutene and identification of possible precursors to the naturally occurring (+)-enantiomer
A chemoenzymatic synthesis of the linear triquinane (-)-hirsutene and identification of possible precursors to the naturally occurring (+)-enantiomer
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DOI：
10.1016/j.tet.2003.10.122
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发表时间：
2004-01-12
期刊：
影响因子：
2.1
通讯作者：
Jolliffe, KA
中科院分区：
文献类型：
--
作者：
Banwell, MG;Edwards, AJ;Jolliffe, KA
对映体纯的顺式-1,2-二氢儿茶酚很容易通过全细胞生物转化过程中甲苯双加氧酶介导的甲苯二羟基化获得，已通过 17 个步骤转化为线性三奎烷 (-)-hirsuten。由于起始材料的对映异构体也是可用的，这项工作构成了天然存在的 (+)-形式的 hirsuten 的正式全合成。此外，对此处使用的路线进行微小修改提供了从原始起始材料获取(+)-hirsuten的可能性。 (C) 2003 Elsevier Ltd. 保留所有权利。
An enantiomerically pure cis-1,2-dihydrocatechol, which is readily obtained via a toluene dioxygenase-mediated dihydroxylation of toluene in a whole-cell biotransformation process, has been converted over 17 steps into the linear triquinane (-)-hirsutene. Since the enantiomer of the starting material is also available this work constitutes a formal total synthesis of the naturally occurring (+)-form of hirsutene. Furthermore, minor modifications of the route used here offer the possibility of accessing (+)-hirsutene from the original starting material. (C) 2003 Elsevier Ltd. All rights reserved.