Chen Sijia, Zhang Zhongchao, Jiang Chongguo, Zhao Chunbo, Luo Haojie, Huang Jun, Yang Zhen
State Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China.
ACS Omega. 2021 Jul 13;6(29):18848-18859. doi: 10.1021/acsomega.1c02054. eCollection 2021 Jul 27.
Diastereoselective synthesis of the -decalin-based α-hydroxyl butanone spirocarbocycles bearing all-carbon quaternary stereogenic centers has been achieved via Norrish-Yang photocyclization of -decalin-substituted-2,3-butanediones using daylight. Density functional theory (DFT) calculations suggest that this diastereoselective reaction is affected by both substrate conformation and intramolecular hydrogen bonds. The developed chemistry could be applied to synthesizing the derivatives of the -decalin-based biologically important natural products.
通过使用日光对十氢化萘取代的2,3-丁二酮进行Norrish-Yang光环化反应，实现了带有全碳季立体中心的基于十氢化萘的α-羟基丁酮螺环碳环的非对映选择性合成。密度泛函理论（DFT）计算表明，这种非对映选择性反应受底物构象和分子内氢键的影响。所开发的化学方法可应用于合成基于十氢化萘的具有重要生物学意义的天然产物的衍生物。
