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Formation of Benzyl Oxazole, A Competitive Path with the Classical Bishler-Napieralski Reaction

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chinese Chemical Letters 2001年第11期12卷 947-950页

作者： zhan zhu liu ye feng tang shi zhi CHEN Institute of materia medica Chinese Academy of Material Sciences&Peking Union Medical CollegeBeijing 100050

Several aromatic ring-substituted N-acetyl-phenylalanine methyl esters were treated with POCl3 in refluxing benzene, which is the typical condition of B-N reaction. It was found that the normal B-N product 3, 4-dihydroisoquinoline-3-carboxylic acid methyl ester and/or 5-benzyl-2-methyl-4-methoxy oxazole could be obtained. The result depended mainly upon the electron-donating property of the substitutes on the benzene ring. Strong electron-donating groups located at para- or ortho- to the cyclization site will facilitate the formation of the normal B-N product 2. On the other hand, the absence or weak electron-donating groups tended to yield the oxazole product 3. It was established that the formation of benzyl oxazole is the competitive path with the B-N reaction. In this article, an explanation was given based on the mechanism of Bishler-Napieralski reaction.

关键词： Bishler-Napieralski reaction benzyl oxazole 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid N-acetyl-phenytalanine methyl ester

Stereospecific Synthesis of the Skeleton of the Antitumor Marine Natural Product Et-743

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Stereospecific Synthesis of the Skeleton of the Antitumor Ma...

An Efficient Synthetic Strategy for Construction of Functionalized Pentacyclic Skeleton of ecteinascidin-saframycin Alkaloids

第三届全国有机化学学术会议

作者： liu, zhan-zhu tang, ye-feng WANG, ye CHEN, shi-zhi (Institute of materia Medina , peking union medical College & chinese academy of medical sciences , beijing 100050)

＜正＞ Ecteinascidin 743 （Et-743） is an exceedingly potent antitumor agent isolated from the marine tunicate Ecteinascidia turbinate . As its structurally simplified version, Phthalascidin was found to retain the cytotoxicity of the natural product. Their novel structures, impressive biological activities and difficult availabilities conspire to render the attractive targets for total synthesis. Corey and co-workers completed the total synthesis of Et-743 and phtha-

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chinese Chemical Letters 2006年第7期17卷 853-856页

作者： ye WANG zhan zhu liu ye feng tang shi zhi CHEN Institute of materia medica Chinese Academy of Medical Sciences ＆ Peking Union Medical College Beijing 100050

Two functionalized pentacyclic compounds 12a, 12b were constructed via a highly efficient synthetic route, employing a tricyclic amino aldehyde as the key intermediate. The crucial steps involved coupling of two segme... 详细信息

关键词： Ecteinascidin saframycin tetrahydroisoquinoline Pictet-Spengler reaction.

Highly Efficient Diastereoselective Synthesis of Tetrahydro-isoquinoline-3-carboxylate Ester Analogs from L-DOPA

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Highly Efficient Diastereoselective Synthesis of Tetrahydro-...

Construction of the Skeleton of Phthalascidin, Mechanism of the Formation of the Key Tricyclic Lactam Intermediate

第三届全国有机化学学术会议

作者： WANG, ye liu, zhan-zhu CHEN, shi-zhi LIANG, Xiao-Tian (Institute of materia medica, peking union medical College & chinese academy of medical sciences , beijing 100050)

＜正＞ Tetrahydroisoquinoline-3-carboxylate esters are an important motif of naturally occurring bioactive alkaloids and pharmacophores. They are generally regarded as neurotoxic compounds and are putatively involved in a variety of pathologic conditions of central nervous system, including alcoholism, phenylketonuria, and neurodegenerative disorders such as Parkinson’s *** our strategy of the synthesis of the anticancer marine alkaloid Ecteinascidin, tetrahydroisoquinoline-3-car-

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chinese Chemical Letters 2002年第8期13卷 701-704页

作者： zhan zhu liu ye WANG shi zhi CHEN Institute of materia medica Chinese Academy of Medical Sciences&Peking Union Medical CollegeBeijing 100050

The mechanism of the formation of a key tricyclic lactam intermediate 3 was studied. It was found that the E-form compound 3 was transformed from the Z-form compound 4. The formation of 4 was a kinetically controlled process while the formation of 3 was a thermodynamically favorable one. A possible mechanism was given in this paper.

关键词： Lactam phthalascidin mechanism Et-743.

Synthesis and Antitumor Activity of an Analog of Phthalascidin

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chinese Chemical Letters 2006年第10期17卷 1279-1282页

作者： ye WANG Yan Li ZHOU zhan zhu liu shi zhi CHEN Xiao Guang CHEN Institute of materia medica Chinese Academy of Medical Sciences ＆ Peking Union Medical College Beijing 100050

An analog of phthalascidin （Pt-650） was synthesized with an improved synthetic route. With precursor 2 as the starting material, compound 1 was prepared through 4 steps in a total yield of 47%. In vitro antitumor test of this Pt-650 analog showed that it possessed strong toxicity against a number of tumor cell lines including A2780, A549, Bel-7402, BGC-823, HELA, KB, KeTr3 and HCT-8.

关键词： Ecteinascidin phthalascidin tetrahydroisoquinoline antitumor.

Stereospecific Synthesis of the Skeleton of the Antitumor Marine Natural Product Et-743

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有机化学 2003年第Z1期23卷 336-336页

作者： liu zhan-zhu tang ye-feng WANG ye CHEN shi-zhi Institute of materia medica Peking Union Medical College & Chinese Academy of Medical Scicnces Beijing 100050 Institute of Materia Medica Peking Union Medical College & Chinese Academy of Medical Scicnces Beijing 100050 Institute of Materia Medica Peking Union Medical College & Chinese Academy of Medical Scicnces Beijing 100050 Institute of Materia Medica Peking Union Medical College & Chinese Academy of Medical Scicnces Beijing 100050

　　Ecteinascidin 743 (Et-743) is an exceedingly potent antitumor agent isolated from the marine tunicate Ecteinascidia turbinate. As its structurally simplified version, Phthalascidin was found to retain the cytotoxicity of the natural product. Their novel structures, impressive biological activities and difficult availabilities conspire to render the attractive targets for total synthesis.……

关键词： biological activities total synthesis natural product antitumor agent

Highly Efficient Diastereoselective Synthesis of Tetrahydro-isoquinoline-3- carboxylate Ester Analogs from L-DOPA

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有机化学 2003年第Z1期23卷 335-335页

作者： WANG ye liu zhan-zhu CHEN shi-zhi LIANG Xiao-Tian Institute of materia medica Peking Union Medical College & Chinese Academy of Medical Sciences Beijing 100050 Institute of Materia Medica Peking Union Medical College & Chinese Academy of Medical Sciences Beijing 100050 Institute of Materia Medica Peking Union Medical College & Chinese Academy of Medical Sciences Beijing 100050 Institute of Materia Medica Peking Union Medical College & Chinese Academy of Medical Sciences Beijing 100050

　　Tetrahydroisoquinoline-3-carboxylate esters are an important motif of naturally occurring bioactive alkaloids and pharmacophores. They are generally regarded as neurotoxic compounds and are putatively involved in a variety of pathologic conditions of central nervous system, including alcoholism, phenylketonuria, and neurodegenerative disorders such as Parkinson's disease.……

关键词： neurodegenerative disorders central nervous system

Feasibility and physics potential of detecting ^(8)B solar neutrinos at JUNO

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chinese Physics C 2021年第2期45卷 93-110页

作者： Angel Abusleme Thomas Adam Shakeel Ahmad Sebastiano Aiello Muhammad Akram Nawab Ali fengpeng An Guangpeng An Qi An Giuseppe Andronico Nikolay Anfimov Vito Antonelli Tatiana Antoshkina Burin Asavapibhop João Pedro Athayde Marcondes de André Didier Auguste Andrej Babic Wander Baldini Andrea Barresi Eric Baussan Marco Bellato Antonio Bergnoli Enrico Bernieri David Biare Thilo Birkenfeld Sylvie Blin David Blum Simon Blyth Anastasia Bolshakova Mathieu Bongrand Clément Bordereau Dominique Breton Augusto Brigatti Riccardo Brugnera Riccardo Bruno Antonio Budano Max Buesken Mario Buscemi Jose Busto Ilya Butorov Anatael Cabrera Hao Cai Xiao Cai Yanke Cai zhiyan Cai Antonio Cammi Agustin Campeny Chuanya Cao Guofu Cao Jun Cao Rossella Caruso Cédric Cerna Jinfan Chang Yun Chang Pingping Chen Po-An Chen Shaomin Chen Shenjian Chen Xurong Chen Yi-Wen Chen Yixue Chen Yu Chen zhang Chen Jie Cheng Yaping Cheng Alexander Chepurnov Davide Chiesa Pietro Chimenti Artem Chukanov Anna Chuvashova Gérard Claverie Catia Clementi Barbara Clerbaux Selma Conforti Di Lorenzo Daniele Corti Salvatore Costa Flavio Dal Corso Christophe De La Taille Jiawei Deng zhi Deng Ziyan Deng Wilfried Depnering Marco Diaz Xuefeng Ding Yayun Ding Bayu Dirgantara Sergey Dmitrievsky Tadeas Dohnal Georgy Donchenko Jianmeng Dong Damien Dornic Evgeny Doroshkevich Marcos Dracos Frédéric Druillole Shuxian Du Stefano Dusini Martin Dvorak Timo Enqvist Heike Enzmann Andrea Fabbri Lukas Fajt Donghua Fan Lei Fan Can Fang Jian Fang Marco Fargetta Anna Fatkina Dmitry Fedoseev Vladko Fekete Li-Cheng feng Qichun feng Richard Ford Andrey Formozov Amélie Fournier Haonan Gan feng Gao Alberto Garfagnini Alexandre Göttel Christoph Genster Marco Giammarchi Agnese Giaz Nunzio Giudice Franco Giuliani Maxim Gonchar Guanghua Gong Hui Gong Oleg Gorchakov Yuri Gornushkin Marco Grassi Christian Grewing Maxim Gromov Vasily Gromov Minghao Gu Xiaofei Gu Yu Gu Mengyun Guan Nunzio Guardone Maria Gul Cong Guo Jingyuan Guo Wanlei Guo Xinheng Guo Yuhang Guo Paul Hackspacher Caren Hagner Ran Han Yan yerevan Physics Institute YerevanArmenia UniversitéLibre de Bruxelles BrusselsBelgium Universidade Estadual de Londrina LondrinaBrazil Pontificia Universidade Catolica do Rio de Janeiro RioBrazil Pontificia Universidad Católica de Chile SantiagoChile Universidad Tecnica Federico Santa Maria ValparaisoChile beijing Institute of Spacecraft Environment Engineering BeijingChina beijing Normal University BeijingChina China Institute of Atomic Energy BeijingChina Institute of High Energy Physics BeijingChina North China Electric Power University BeijingChina School of Physics Peking UniversityBeijingChina Tsinghua University BeijingChina University of chinese academy of sciences BeijingChina Jilin University ChangchunChina College of Electronic Science and Engineering National University of Defense TechnologyChangshaChina Chongqing University ChongqingChina Dongguan University of Technology DongguanChina Jinan University GuangzhouChina Sun Yat-Sen University GuangzhouChina Harbin Institute of Technology HarbinChina University of Science and Technology of China HefeiChina The Radiochemistry and Nuclear Chemistry Group in University of South China HengyangChina Wuyi University JiangmenChina Shandong University JinanChina Institute of Modern Physics Chinese Academy of SciencesLanzhouChina Nanjing University NanjingChina Guangxi University NanningChina East China University of Science and Technology ShanghaiChina School of Physics and Astronomy Shanghai Jiao Tong UniversityShanghaiChina Tsung-Dao Lee Institute Shanghai Jiao Tong UniversityShanghaiChina Institute of Hydrogeology and Environmental Geology Chinese Academy of Geological SciencesShijiazhuangChina Nankai University TianjinChina Wuhan University WuhanChina Xi’an Jiaotong University Xi’anChina Xiamen University XiamenChina School of Physics and Microelectronics Zhengzhou UniversityZhengzhouChina Institute of Physics National Chiao-Tung University Hsinchu National United University Miao-Li Department of Physics National T

The Jiangmen Underground Neutrino Observatory(JUNO)features a 20 kt multi-purpose underground liquid scintillator sphere as its main *** of JUNO's features make it an excellent location for^8B solar neutrino measurements,such as its low-energy threshold,high energy resolution compared with water Cherenkov detectors,and much larger target mass compared with previous liquid scintillator *** this paper,we present a comprehensive assessment of JUNO's potential for detecting^8B solar neutrinos via the neutrino-electron elastic scattering process.A reduced 2 MeV threshold for the recoil electron energy is found to be achievable,assuming that the intrinsic radioactive background^(238)U and^(232)Th in the liquid scintillator can be controlled to 10^(-17)g/*** ten years of data acquisition,approximately 60,000 signal and 30,000 background events are *** large sample will enable an examination of the distortion of the recoil electron spectrum that is dominated by the neutrino flavor transformation in the dense solar matter,which will shed new light on the inconsistency between the measured electron spectra and the predictions of the standard three-flavor neutrino oscillation *** m^(2)_(21)=4.8times10^(-5);(7.5times10^(-5))eV^(2),JUNO can provide evidence of neutrino oscillation in the Earth at approximately the 3sigma(2sigma)level by measuring the non-zero signal rate variation with respect to the solar zenith ***,JUNO can simultaneously measureDelta m^2_(21)using^8B solar neutrinos to a precision of 20% or better,depending on the central value,and to sub-percent precision using reactor antineutrinos.A comparison of these two measurements from the same detector will help understand the current mild inconsistency between the value of Delta m^2_(21)reported by solar neutrino experiments and the KamLAND experiment.

关键词： neutrino oscillation solar neutrino JUNO