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Recently, Professor Ye Longwu and Professor Lv Xin of the school of chemistry and chemical engineering of Xiamen University have made new progress in the research of heterocyclic synthesis methodology based on alkynamide The related achievements are published online in angel Chem under the title of "organic energetic selective conia ene type carbocyclization of dynamic cycloxanones: regional synthesis of morphans and normorphans" Int Ed (DOI: 10.1002/anie.201908495)。
The heterocyclic skeletons of morphan and normorphan exist widely in bioactive molecules and natural products Therefore, the research on the synthesis methods of these two kinds of AZA bridged molecules has always been the focus of organic synthesis However, how to realize the asymmetric synthesis of these two kinds of molecules is still a challenge In addition, conia ene reaction has attracted a lot of attention in recent years, especially the asymmetric conia ene reaction based on alkynes can be realized by bimetallic catalysis or metal and organic small molecule synergistic catalysis However, these methods are only limited to metal catalysis, and no metal catalysis has been reported In recent years, Professor Ye Longwu's research group has developed a series of new series reactions based on alkynamide oxidation, amination, cycloisomerization and so on, which provide a new way for the diversity synthesis of a series of functional heterocycles and apply it to the efficient and concise synthesis of dozens of natural products, bioactive molecules and drugs Relevant research results were published in NAT Commun., J am Chem SOC., angel Chem Int ed., chem SCI., etc However, these series reactions are limited to Lewis acid or br ø nsted Acid Catalysis, and no asymmetric catalysis has been reported Recently, Professor Ye Longwu's research group has successfully realized the asymmetric conia ene reaction catalyzed by small organic molecules with cyclohexanone modified alkynamide as the substrate, and constructed a series of chiral azabridged molecules with high efficiency This reaction has the following characteristics: (1) for the first time, a metal free asymmetric conia ene reaction has been realized, and an organic small molecule catalyzed asymmetric reaction of alkynamide has been realized( 2) The reaction can synthesize morphan with excellent yield and enantioselectivity, and the substrate has wide universality; (3) the chiral normorphan can be obtained with high regioselectivity by changing the protecting group on the alkynamide nitrogen; (4) the two kinds of products can be obtained by subsequent multi-step derivatization, and more than half of them have antitumor activity; (5) )DFT calculation explains the mechanism of this kind of reaction, and clarifies the origin of regioselectivity and enantioselectivity control The research work is mainly completed by Professor Ye Longwu's 2016 master student Xu Yin (now 2019 doctoral student), and assisted by other graduate students and undergraduates of the research team The theoretical calculation was completed by sun Qing, a research group of Professor Lu Xin, and the single crystal analysis was assisted by Yuan Peng, a doctoral student of the research group of Professor Zheng Nanfeng Professor Deng Xianming's research group of Xiamen University provided help in biological activity test and single crystal test by Wei zanbin, engineer of School of chemical engineering The research work was supported by the National Natural Science Foundation of China (21622204, 91545105, 21772161), the president's fund of Xiamen University (20720180036), the National Basic Science Talent Training Fund (j1310024), the Yangtze River scholars and innovation team development plan of the Ministry of education, etc.