Rhodomentosones A and B: Two Pairs of Enantiomeric Phloroglucinol Trimers from Rhodomyrtus tomentosa and Their Asymmetric Biomimetic Synthesis
Rhodomentosones A and B: Two Pairs of Enantiomeric Phloroglucinol Trimers from Rhodomyrtus tomentosa and Their Asymmetric Biomimetic Synthesis
复制标题
红桃酮 A 和 B：毛红桃中的两对对映体间苯三酚三聚体及其不对称仿生合成
DOI：
10.1021/acs.orglett.1c01616
复制
发表时间：
2021-05-25
期刊：
影响因子：
5.2
通讯作者：
Wang, Ying
中科院分区：
文献类型：
--
作者：
Deng, Lu-Ming;Hu, Li-Jun;Wang, Ying
从桃金娘（Rhodomyrtus tomentosa）中分离得到两对具有独特6/5/5/6/5/5/6稠环结构的间苯三酚三聚体--桃金娘酮A和B（1和2）。通过核磁共振谱、X-射线晶体学和电子捕获度计算确定了它们的绝对构型。1和2的生物启发合成在六个步骤中实现，其特征在于有机催化的不对称脱羟基/Michael加成/Kornblum-DeLaMare重排/缩酮化级联反应。化合物1和2对呼吸道合胞病毒（RSV）具有较好的抗病毒活性。
Rhodomentosones A and B (1 and 2), two pairs of novel enantiomeric phloroglucinol trimers featuring a unique 6/5/5/6/5/5/6-fused ring system were isolated from Rhodomyrtus tomentosa. Their structures with absolute configurations were elucidated by NMR spectroscopy, X-ray crystallography, and ECD calculation. The bioinspired syntheses of 1 and 2 were achieved in six steps featuring an organocatalytic asymmetric dehydroxylation/Michael addition/Kornblum-DeLaMare rearrangement/ketalization cascade reaction. Compounds 1 and 2 exhibited promising antiviral activities against respiratory syncytial virus (RSV).