Syntheses of taiwaniaquinone F and taiwaniaquinol A via an unusual remote C-H functionalization.

Syntheses of taiwaniaquinone F and taiwaniaquinol A via an unusual remote C-H functionalization.
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DOI：
10.1021/ol4003652
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发表时间：
2013-03
期刊：
Organic letters
影响因子：
5.2
通讯作者：
C. Thommen;C. Jana;M. Neuburger;K. Gademann
C. Thommen;C. Jana;M. Neuburger;K. Gademann
中科院分区：
化学1区
文献类型：
--
作者：
C. Thommen;C. Jana;M. Neuburger;K. Gademann

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报道了一种基于糖醇衍生物的环收缩和随后的芳族氧化的无保护基的（-）-台湾醌F的路线。此外，首次报道了通过（-）-台湾醌F短时间暴露于阳光引发远程C-H官能化来合成（+）-台湾醌醇A。一些亚甲二氧基桥接的天然产物的生物合成可以通过类似的非酶机制的假设。
A protecting-group-free route to (-)-taiwaniaquinone F based on a ring contraction and subsequent aromatic oxidation of a sugiol derivative is reported. In addition, the first synthesis of (+)-taiwaniaquinol A is reported via short time exposure of (-)-taiwaniaquinone F to sunlight triggering a remote C-H functionalization. The hypothesis that the biogenesis of some methylenedioxy bridged natural products could proceed via similar nonenzymatic mechanisms is presented.