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红花远志素 A 和 B: 和 的两对对映异构间苯三酚三聚体及其不对称仿生合成。

Rhodomentosones A and B: Two Pairs of Enantiomeric Phloroglucinol Trimers from and Their Asymmetric Biomimetic Synthesis.

机构信息

Center for Bioactive Natural Molecules and Innovative Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, People's Republic of China.

Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research, Jinan University, Guangzhou 510632, People's Republic of China.

出版信息

Org Lett. 2021 Jun 4;23(11):4499-4504. doi: 10.1021/acs.orglett.1c01616. Epub 2021 May 25.

DOI:10.1021/acs.orglett.1c01616
PMID:34032453
Abstract

Rhodomentosones A and B ( and ), two pairs of novel enantiomeric phloroglucinol trimers featuring a unique 6/5/5/6/5/5/6-fused ring system were isolated from . Their structures with absolute configurations were elucidated by NMR spectroscopy, X-ray crystallography, and ECD calculation. The bioinspired syntheses of and were achieved in six steps featuring an organocatalytic asymmetric dehydroxylation/Michael addition/Kornblum-DeLaMare rearrangement/ketalization cascade reaction. Compounds and exhibited promising antiviral activities against respiratory syncytial virus (RSV).

摘要

红树酮 A 和 B(和),一对新型对映体间苯三酚三聚体,具有独特的 6/5/5/6/5/5/6 稠合环系统,从红树植物中分离得到。通过核磁共振波谱、X 射线晶体学和圆二色性计算确定了它们的结构和绝对构型。和的生物启发全合成通过有机催化不对称去羟化/Michael 加成/Kornblum-DeLaMare 重排/缩酮化级联反应在六步中实现。化合物和表现出对呼吸道合胞病毒(RSV)有良好的抗病毒活性。

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