Synthesis and antibacterial activity of 6(R)- and 6(S)-fluoropenibruguieramine As: Fluorine as a probe for testing the powerfulness of memory of chirality (MOC)
Synthesis and antibacterial activity of 6(R)- and 6(S)-fluoropenibruguieramine As: Fluorine as a probe for testing the powerfulness of memory of chirality (MOC)
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DOI：
10.1016/j.jfluchem.2018.01.002
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发表时间：
2018-03-01
影响因子：
1.9
通讯作者：
Hu, Xiang-Guo
中科院分区：
文献类型：
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作者：
Liu, Ting;Yan, Nan;Hu, Xiang-Guo
6(R)-和6(S)-氟openibruguieramine As的合成已经完成，采用了Kim及其同事开发的优雅策略。通过关键的分子内醛醇反应形成了单一的非对映体，两种产物均通过x射线衍射晶体学得到了明确的证实。该反应表明氟酰胺效应无法与手性记忆（MOC）效应竞争，从而进一步证明了MOC效应在不对称合成中的强大作用。本工作进行的生物学试验表明，天然提取物抑菌活性的主要成分可能不是penibruguieramine A。
The synthesis of 6(R)- and 6(S)-fluoropenibruguieramine As has been achieved, employing the elegant strategy developed by Kim and co-workers. Single diastereomers were formed via the key intramolecular aldol reaction, and both of the products were unambiguously confirmed by X-ray diffraction crystallography. This reaction shows that the fluorine amide effect could not compete with the memory of chirality (MOC) effect, thus further demonstrating the powerfulness of MOC effect in asymmetric synthesis. The biological testing carried out in this work indicates that the principal of antibacterial activity of the natural extract is probably not penibruguieramine A.