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total synthesis of Marine Cyclic Enol-Phosphotriester Salinipostin Compounds

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Journal of Ocean University of China 2018年第3期17卷 683-689页

作者： ZHAO Mingliang WEI Xianfeng LIU Xuemeng DONG Xueyang YU Rilei WAN Shengbiao JIANG Tao Key Laboratory of Marine Drugs The Ministry of Education of China School of Medicine and Pharmacy Ocean University of China Laboratory for Marine Drugs and Bioproducts Qingdao National Laboratory for Marine Science and Technology

Due to their structural diversity and variety of biological activities, marine natural products have been the subject of extensive study. These compounds, especially phospholipid polycyclic aromatic hydrocarbons, have a wide range of pharmacological applications, including embedded DNA and central nervous system, anti-tumor, anti-virus, anti-parasite, anti-bacterial, and antithrombotic effects. Unfortunately, the insufficient drug sources have limited the development of these compounds. In this study, we isolated salinpostin compounds from a fermentation solution of marine-derived Salinospora sp., which has a common bicyclic enol-phosphotriester core framework, as well as potent and selective antimalarial activities against P. falciparum with EC_(50)=50 nmolL^(-1). The chemical synthesis of these compounds in greater quantities is necessary for their use in bioactivity studies. Thus we explored a short route with high yields and mild reaction conditions, which can generate combinatorial libraries for drug discovery and lead optimization. We developed a new total synthesis method for six cyclic enol-phosphotriester salinipotin compounds and their diastereomers. For the total synthesis of cyclipostin P, we prepared cyclic enol-phosphotriester salinipostin compounds in 10 steps from a readily accessible starting material, 1,3-dihydroxyacetone, and obtained an overall yield of 1.29%. We fully characterized these compounds by proton nuclear magnetic resonance(~1H-NMR), carbon-13 NMR(^(13)C-NMR), and high-resolution mass spectrometry(HRMS) analyses, and found they coincide absolutely with the same compounds reported previously.

关键词： total synthesis Salinipostin enolphosphate trimester

total synthesis of Starfish Cyclic Steroid *** 1,synthesis of the Aglycone and Attempts at Installation of the Sugar Units

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Chinese Journal of Chemistry 2023年第8期41卷 891-896页

作者： Bingfeng Shi Youxi Chen Mingyu Geng Dapeng Zhu Biao Yu State Key Laboratory of Bioorganic and Natural Products Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai200032 China Department of Chemistry Zhejiang UniversityHangzhouZhejiang310027 China

Comprehensive Summary Sepositoside A(1)is the major and first cyclic steroid glycoside isolated from starfishes,which features a strained 16-membered ring formed by tethering C3 and C6 of the steroid aglycone with a linear *** conceived a convergent synthetic plan in which sepositoside A was disconnected into a disaccharide and a steroid-glucose hybrid *** desired 3β,6β-dihydroxy-Δ7,8-23-one aglcyone was readily prepared from dehydroepiandrosterone in 12 *** etherification of the 6β-hydroxy-Δ7,8-steroid with a variety of hexopyranoside-C6-electrophiles and CO_(2)-extrusion of a steroid-pyranose hybrid carbonate were extensively studied;however,formation of the desired steroid-pyranose etherate linkage has not been *** studies on theβ-selective installation of the(1→2)-linked disaccharide onto the steroidal C3β-OH with the corresponding disaccharideα-imidates were also examined,however,formation of theα-glycosides *** present results force us to explore alternative approaches to construct the steroid-pyranose etherate linkage and stepwise assembly of the glycans en route to the starfish cyclic steroid glycosides,which will be presented in two articles that follow.

关键词： Cyclic starfish glycosides Etherification Glycosylation Steroid total synthesis

total synthesis of Syringin and Its Natural Analogues via C—C Bond Activation of Aryl Ketones

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Chinese Journal of Chemistry 2023年第24期41卷 3587-3592页

作者： Zhen-Yu Wang Yi Sun Guo-Dong Sun Hui Xu Hui-Xiong Dai School of Chinese Materia Medica Nanjing University of Chinese MedicineNanjingJiangsu210023 China CAS Key Laboratory of Receptor Research State Key Laboratory of Drug ResearchShanghai Institute of Materia MedicaChinese Academy of SciencesShanghai201203 China University of Chinese Academy of Sciences Beijing100049 China

Syringin is found in the root of Acanthopanax senticosus(***.)Harms and belongs to the lignin chemical compound with many biological *** this study,we employed commercially available starting materials and accomplished the total synthesis of syringin in 5 steps with an overall yield of 58%.Palladium-catalyzed C(O)–C bond activation and subsequent cross coupling reaction is the key to construct syringin and its natural analogues.

关键词： Syringin total synthesis Cross-coupling C—C activation Syringin analogues

total synthesis of Nucleoside Antibiotics Amicetin,Plicacetin,and Cytosaminomycin A-D

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Chinese Journal of Chemistry 2021年第10期39卷 2679-2684页

作者： Jiqiang Fu Peng Xu Biao Yu State Key Laboratory of Bioorganic and Natural Products Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling RoadShanghai200032 China School of Chemistry and Materials Science Hangzhou Institute for Advanced StudyUniversity of Chinese Academy of Sciences1 Sub-lane XiangshanHangzhouZhejiang310024 China

Main observation and conclusion Amicetin and congeners constitute a small family of complex pyrimidine nucleosides,which exhibit strong antibiotic activities against Gram-positive bacteria and notably against strains of Mycobacterium ***,we report chemical synthesis of a series of disaccharide congeners of the amicetin family,including amicetin,plicacetin,and cytosaminomycin A—*** is the first time for successful synthesis of amicetin,the prototypical member,and *** synthetic approach employs glycosyl N-phenyltrifluoroacetimidate and thioglycoside donors to construct the characteristic aminodeoxydisaccharides consisting ofα-(1→4)-glycosidic linkage,uses gold(I)-catalyzed N-glycosylation to furnish 2-deoxy-β-nucleosides,and finally exploits amidation and global deprotection to complete the *** is noteworthy that the 3-O-protecting group in the 2-deoxydisaccharide donors is found to be crucial for a successful N-glycosylation to assemble the cytosaminomycin disaccharide nucleosides.

关键词： total synthesis Glycosylation Nucleoside Amicetin Cytosaminomycin

total synthesis of UCS1025A via Tandem Carbonylative Stille Cross Coupling and Diels-Alder Reactiont

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Chinese Journal of Chemistry 2023年第22期41卷 3019-3024页

作者： Chengsen Cui Mingi Dai Deparment of Chemistry and Center for Cancer Research Purdue University West Lfaytte IN 47907United States Department of Chemistry Emory UniversityAtlantaGA 30322United States

We report an efficient and convergent strategy for the total synthesis of UCS1025A and its diastereomer ***1025A is a representative member of the naturally occurring pyrrolizidinone polyketides,from which members with potent antibacterial,antifungal,and anticancer activities have been *** approach features a tandem carbonylative Stille cross coupling and Diels-Alder reaction to forge a key C-C bond and build the trans-decalin *** tandem process utilizes carbon monoxide as a one-carbon linchpin to stitch a vinyl triflate and a vinylstannane together and form the desired enone moiety for the subsequent intramolecular Diels-Alder *** synthesis also provides a versatile approach for the synthesis of other related pyrrolizidinone-containing polyketides.

关键词： Natural products total synthesis UCS1025A Carbonylation Diels-Alder reaction Tandem reaction

total synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

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Chinese Journal of Chemistry 2024年第11期42卷 1267-1274页

作者： Yuye Chen Wenqing Chen Zhiting Zhang Jing Xu Shenzhen Grubbs Institute and Department of Chemistry and Guangming Advanced Research Institute and Guangdong Provincial Key Laboratory of Catalysis and Shenzhen Key Laboratory of Small Molecule Drug Discovery and synthesis Southern University of Science and TechnologyShenzhenGuangdong518055 China

As one of the most common structural motifs in natural products,cyclopentenones usually can be fabricated by Nazarov cyclization using divinyl ketones or functionalized tertiary divinyl carbinols(TDCs)as ***,straightforward method for transforming unfunctionalized TDCs to their corresponding cyclopentenones is currently ***,we wish to report the total syntheses of four structurally distinct terpenoids,namely laurane-type marine sesquiterpenoids isolaurene,debromoaplysin and aplysin,and guaiane sesquiterpenoid guaiadienone A,all using a novel synthetic method,named oxidative Nazarov cyclization,as the key *** work demonstrated our robust method is suitable for synthesizing various highly substituted cyclopentenones.

关键词： total synthesis Synthetic methods Sesquiterpenoids Oxidative Nazarov reaction Electrocyclization Oxoammonium salt Pericyclic reaction Annulation

total synthesis and anticancer activity studies of the stereoisomers of asperphenamate and patriscabratine

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Chinese Chemical Letters 2010年第2期21卷 155-158页

作者： Yuan, Lei Wang, Jin Hui Sun, Tie Min Shenyang Pharmaceut Univ Sch Pharmaceut Engn Shenyang 110016 Peoples R China Shenyang Pharmaceut Univ Sch Traditt Chinese Mat Med Shenyang 110016 Peoples R China

All stereoisomers of asperphenamate 1a and patriscabratine 2a were achieved with a high yield,and total synthesis of 2a is firstly described *** absolute configuration of patriscabratine was determined as(S,S).The compounds 1a-d and 2a-d have been tested by MTT assay in T47D,MDA-MB231,HL60,Hela and SGC-7901 cell lines in *** them,the(R,S) stereoisomer shows the strongest anticancer effects,while the(S,R) shows the weakest one.

关键词： N N -substituted phenylalanine-phenylalaninol ester Asperphenamate Patriscabratine total synthesis Anticancer activity

total synthesis and Stereochemical Assignment of Talaroconvolutin A and Talarofuranone: Gram-scale synthesis of Ferroptosis Inducer Talaroconvolutin A

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Chinese Journal of Chemistry 2024年第13期42卷 1509-1514页

作者： Ming Yao Wei Yang Jing Li Chengyun Huang Jin Fang Sulu Qin Shuzhi Liu Xiaolong Yang School of Pharmaceutical Sciences South-Central Minzu UniversityWuhanHubei 430074China

The first total synthesis of talaroconvolutin A(1.1 g obtained)and talarofuranone has been achieved using accessible materials(12 steps,7.5%and 8.2%yields,respectively).Convergent routes involved intramolecular Diels-Alder reactions in two approaches for creating the decalin ***,an unprecedented DMP-mediated domino reaction resulted in the deoxy-tetramic acid *** syntheses not only establish the absolute configuration of talaroconvolutin A but also enable further collaborative studies of this typeofferroptosisinducers.

关键词： Natural products Aldehydes total synthesis Domino reactions Biological activity Antitumor agents Ferroptosis Diels-Alder reaction Talaroconvolutin A

total synthesis and Biological Evaluation of Wewakazole

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Chemical Research in Chinese Universities 2017年第6期33卷 890-894页

作者： LONG Bohua ZHANG Jingzhao WANG Xueyan TANG Xudong WU Zhengzhi The Fourth People's Hospital ofShenzhen Shenzhen 518033 P. R. China Shenzhen Institute of Geriatncs Shenzhen 518020 P. R. China The Second People's Hospital of Shenzhen Shenzhen 518035 P. R. China Key Lab for New Drug Research of TCM and Shenzhen Branch State R&D Centre for Viro-Biotech Research Institute of Tsinghua University in Shenzhen Shenzhen 518057 P. R. China

The total synthesis of Wewakazole was achieved on a gram scale, unambiguously confirming its structure. Three different substituted oxazoles present in this natural product were prepared efficiently. Biological evalua... 详细信息

关键词： Wewakazole total synthesis Biological evaluation