通过激发态纳扎罗夫反应立体选择性合成吡咯烷类和渥曼青霉素类的核心结构。
Stereoselective Synthesis of the Core Structures of Pyrrocidines and Wortmannines through the Excited-State Nazarov Reactions.
作者信息
Xue Dongsheng, Que Yonglei, Shao Hao, He Haibing, Zhao Xiaoli, Gao Shuanhu
机构信息
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.
出版信息
Org Lett. 2021 Apr 2;23(7):2736-2741. doi: 10.1021/acs.orglett.1c00643. Epub 2021 Mar 24.
The reaction conditions and scope of the excited-state Nazarov reaction of dicyclicvinyl ketones were studied. The stereochemistry of this electrocyclization is consistent with the mechanism of the pericyclic reaction and Woodward-Hoffmann rule. UV-light-promoted excited-state Nazarov reactions gave hydrofluorenones bearing a configuration via a disrotatory cyclization. The core tricyclic hydrofluorenones of pyrrocidines and wortmannines were constructed via the excited-state Nazarov reactions, which demonstrated their synthetic potential in complex natural product total synthesis.
研究了双环乙烯基酮激发态纳扎罗夫反应的反应条件和范围。该电环化反应的立体化学与周环反应机理和伍德沃德-霍夫曼规则一致。紫外光促进的激发态纳扎罗夫反应通过对旋环化生成具有特定构型的氢化芴酮。通过激发态纳扎罗夫反应构建了吡咯西定和渥曼青霉素的核心三环氢化芴酮，这证明了它们在复杂天然产物全合成中的合成潜力。
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