Isolation and biomimetic total synthesis of tomentodiones A-B, terpenoid-conjugated phloroglucinols from the leaves of Rhodomyrtus tomentosa
Isolation and biomimetic total synthesis of tomentodiones A-B, terpenoid-conjugated phloroglucinols from the leaves of Rhodomyrtus tomentosa
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毛红桃叶中毛二酮 A-B、萜类化合物间苯三酚的分离和仿生全合成
DOI：
10.1039/c6ra08776k
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发表时间：
2016-01-01
期刊：
影响因子：
3.9
通讯作者：
Qiu, Sheng-Xiang
中科院分区：
文献类型：
--
作者：
Liu, Hong-Xin;Chen, Kai;Qiu, Sheng-Xiang
Tomentodiones A (1) 和 B (2) 是一对石竹烯缀合间苯三酚的 C-110 差向异构体，具有前所未有的骨架，是从毛白桃树的叶子中分离出来的。通过应用广泛的光谱测量阐明了它们的结构，并通过单晶 X 射线衍射分析和电子圆二色性 (ECD) 计算确定了 1 的绝对构型。提出1和2的生物发生途径以分子间反电子需求Diels-Alder环加成反应为关键步骤，并完成了它们的仿生全合成。
Tomentodiones A (1) and B (2), a pair of C-110 epimers of caryophyllene-conjugated phloroglucinols with an unprecedented skeleton, were isolated from the leaves of Rhodomyrtus tomentosa. Their structures were elucidated through the application of extensive spectroscopic measurements with the absolute configuration of 1 determined by single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD) calculations. The biogenetic pathways of 1 and 2 were proposed to involve an intermolecular, inverse electron demand Diels-Alder cycloaddition reaction as the key step, and their biomimetic total synthesis was accomplished.