倍半萜
立体化学
化学
仿生合成
双环分子
全合成
立体选择性
癸烷
紫茎泽兰
青蒿
神经保护
有机化学
植物
青蒿素
生物
药理学
催化作用
免疫学
疟疾
恶性疟原虫
作者
Bo Yin,Xiaohuan Li,Zixiang Li,Xiaoxin Zhu,Lan Zhang,Xian‐Li Zhou,Jin‐Bu Xu,Feng‐Zheng Chen,Pei Tang,Feng Gao
标识
DOI:10.1002/anie.202306326
摘要
(-)-Adenophorone (1), a caged polycyclic sesquiterpene featuring an unprecedented tricyclo[4.3.1.05,9 ]decane skeleton, was isolated from Eupatorium adenopharum Spreng. The structure of 1 was unambiguously established by a combination of spectroscopic analysis, X-ray crystallography, and bioinspired total synthesis. Key synthetic features include a sequential Reformatsky/oxidation/regio- and stereoselective hydrogenation, and subsequent merged MBH-Tsuji-Trost cyclization. The concise synthetic sequence efficiently constructs the bicyclic skeleton of cadinene sesquiterpene (+)-euptox A (2) in 8 steps from commercially available monoterpene (-)-carvone (6), with outstanding performance on diastereocontrol. The bioinspired synthesis of 1 was achieved from 2, a plausible biogenetic precursor, via transannular Michael addition. This work provides experimental evidence of our proposed biosynthetic hypothesis of 1. Additionally, compound 1 showed potent neuroprotective activity in H2 O2 -treated SH-SY5Y and PC12 cells.
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