Gymnothelignans A-O: conformation and absolute configuration analyses of lignans bearing tetrahydrofuran from Gymnotheca chinensis.
Gymnothelignans A-O: conformation and absolute configuration analyses of lignans bearing tetrahydrofuran from Gymnotheca chinensis.
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DOI：
10.1021/jo301225v
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发表时间：
2012-09
期刊：
影响因子：
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通讯作者：
Dahai He;L. Ding;Hong-Xi Xu;Xinxiang Lei;Hongping Xiao;Yan Zhou
中科院分区：
文献类型：
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作者：
Dahai He;L. Ding;Hong-Xi Xu;Xinxiang Lei;Hongping Xiao;Yan Zhou
从 Gymnotheca chinensis Decne 中分离出 15 种新木酚素，Gymnotheligans A-O (1-15)，带有四氢呋喃，具有可变构象，属于三个潜在相关的骨架。通过详细的光谱分析阐明了结构。使用 X 射线单晶衍射和化学转化确定绝对构型。此外，通过同源性，证实化合物1-11和Eupomatilones在C-5处具有一致的R构型。然而，合成的同系物长期以来被误认为是eupomatilone-6的5-差向异构体。该工作为具有反式H-4-H-5构型的亚eupomatilone家族的绝对构型建立提供了指导。
Fifteen new lignans, gymnothelignans A-O (1-15), bearing tetrahydrofuran with variable conformations belonging to three potentially related skeletons were isolated from Gymnotheca chinensis Decne. The structures were elucidated by means of detailed spectroscopic analysis. Absolute configurations were assigned using X-ray single-crystal diffraction and chemical transformations. Moreover, by the homology, compounds 1-11 and eupomatilones were confirmed to have uniform R-configuration at C-5. However, a synthesized congener has long been mistaken as 5-epimer of eupomatilone-6. This work provides guidance for the absolute configuration establishment of the subeupomatilone family with trans-H-4-H-5 configuration.