Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, China.
Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, School of Chemistry and Molecular Engineering, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, China.
Chem Commun (Camb). 2022 Mar 29;58(26):4239-4242. doi: 10.1039/d2cc00947a.
We report herein a concise total synthesis of streptovertidione, and its transformation to streptovertidine A and formicapyridine A through a bioinspired pyridination. This strategy features: (1) a one-pot Ti(O-Pr)-mediated photoenolization/Diels-Alder (PEDA) reaction/oxidative aromatization sequence for the construction of -dimethyl-anthracenone, a naturally occurring antibiotic pharmacophore; (2) a late-stage pyridination based on the biosynthetic hypothesis. This efficient route supports the preparation of other formicapyridines and derivatives.
我们在此报告了streptovertidione 的简洁全合成，以及通过生物启发的吡啶化将其转化为streptovertidine A 和 formicapyridine A。该策略的特点是：（1）一锅 Ti(O-Pr)介导的光烯醇化/Diels-Alder（PEDA）反应/氧化芳构化序列，用于构建天然存在的抗生素药效团 -二甲基-蒽酮；（2）基于生物合成假设的晚期吡啶化。这种高效的路线支持其他 formicapyridines 和衍生物的制备。
