区域选择性
反应性(心理学)
取代基
化学
组合化学
天然产物
脚手架
结核分枝杆菌
立体化学
表面改性
有机化学
肺结核
催化作用
计算机科学
医学
替代医学
物理化学
病理
数据库
作者
Yolanda Kleiner,Armin Bauer,Peter Hammann,Sören M. M. Schuler,Christoph Pöverlein
出处
期刊:Chemistry
[MDPI AG]
日期:2023-01-16
卷期号:5 (1): 168-178
标识
DOI:10.3390/chemistry5010014
摘要
The recently discovered natural product (NP) (+)-floyocidin B with antimicrobial activity against Mycobacterium tuberculosis displays a hitherto unknown dihydroisoquinolinone scaffold in the class of the epoxyquinone NPs. The 4,5-regioselective functionalization of 2-chloropyridines was identified as a suitable strategy leading to the total syntheses of (+)-floyocidin B and analogs. In this paper, we present the long and winding evolution process to the final synthetic pathway, including model systems for route scouting and elucidation of side products, which enabled us to understand the unique reactivity of this unprecedented scaffold. A special focus was laid on method studies with different 2-chloropyridines, disclosing an unexpected effect of the 2-chloro substituent on the regioselectivity compared to 2-unsubstituted or carbon-substituted pyridines. Finally, a head-to-head comparison with the previously described synthesis of all four stereoisomers of the NP (−)-avicennone C revealed significant differences in the reactivity of these structurally closely related scaffolds.
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