Discovery and Biomimetic Synthesis of a Polycyclic PolymethylatedPhloroglucinol Collection fromRhodomyrtus tomentosa
Discovery and Biomimetic Synthesis of a Polycyclic PolymethylatedPhloroglucinol Collection fromRhodomyrtus tomentosa
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毛红桃中多环多甲基化间苯三酚系列的发现和仿生合成
DOI：
10.1021/acs.joc.2c00071
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发表时间：
2022-04-01
影响因子：
3.6
通讯作者：
Wang, Ying
中科院分区：
文献类型：
--
作者：
Deng, Lu-Ming;Tang, Wei;Wang, Ying
受先前报道的仿生合成研究的启发，从tomentosa中分离出四种新的天然间苯三酚三聚体1-4，它们具有不寻常的6/5/5/6/6/6 /6-融合的六环体系，以及两种已知的类似物（5和6）和两种已知的生物遗传学相关的二聚体（10和11）。通过光谱分析、x射线衍射和电子圆二色性计算，明确了它们的结构和绝对构型。通过模拟两种可能替代的生物合成途径，第一个不对称合成1-4和外消旋合成5和6只需要5到6个步骤，而不需要保护基团。此外，间苯三酚二聚体10和11对呼吸道合胞病毒表现出显著的体外抗病毒活性。
Inspired by a previously reported biomimetic synthesis study, four new naturally occurring phloroglucinol trimers1-4with unusual 6/5/5/6/6/6-fused hexacyclic ring systems, along with two known analogues (5and6) and two knownbiogenetically related dimers (10and11), were isolated fromRhodomyrtus tomentosa. Their structures and absolute configurationswere unambiguously elucidated by spectroscopic analysis, X-ray diffraction, and electronic circular dichroism calculation. Bymimicking two potentially alternative biosynthetic pathways, thefirst asymmetric syntheses of1-4and the racemic syntheses of5and6were achieved in onlyfive to six steps without the need for protecting groups. Furthermore, phloroglucinol dimers10and11exhibited significant in vitro antiviral activity against the respiratory syncytial virus.