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Strategies for constructing seven-membered rings:Applications in natural product synthesis

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Chinese Chemical Letters 2024年第6期35卷 53-70页

作者： peng Chen Lijuan Liang Yufei Zhu Zhimin Xing Zhenhua Jia teck-peng loh College of Advanced Interdisciplinary Science and Technology Henan University of TechnologyZhengzhou 450001China Division of Chemistry and Biological Chemistry School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Nanjing Tech UniversityNanjing 211816China State Key Laboratory of Applied Organic Chemistry Department of ChemistryLanzhou UniversityLanzhou 730000China

The seven-membered ring motifs are found in bioactive pharmaceuticals and a wide range of natural products,including alkaloids and terpenoids,which hold significant importance in synthetic chemistry and has garnered considerable attention from both academia and *** the challenges faced in the past decade,the total synthesis of natural products incorporating the non-aromatic cycloheptane skeletons remains a compelling ***,numerous elegant strategies for constructing the sevenmembered ring system have been successfully *** review focuses on the recent advancements in this field from 2017 to April 2023,highlighting key transformations utilized to construct the non-aromatic cycloheptane core structures and serves as a valuable guide for synthetic chemists engaged in the total synthesis of natural products containing seven-membered ring motifs.

关键词： Seven-membered rings Total synthesis Natural products Synthetic strategy Cycloheptane

Development of catalyst-free carbon-sulfur bond formation reactions under aqueous media and their applications

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Green Synthesis and Catalysis 2022年第4期3卷 309-316页

作者： Min Sun Kang Joycelyn Yi Xin Khoo Zhenhua Jia teck-peng loh Division of Chemistry and Biological Chemistry School of ChemistryChemical Engineering and Biotechnology(CCEB)Nanyang Technological UniversitySingapore 637371Singapore Henan University of Technology 100 Lianhua StZhongyuan DistrictZhengzhou 450001China

Methods for the carbon-sulfur bond formation under catalyst-free,aqueous conditions are extremely useful in organic synthesis and chemical *** laboratory has developed methodologies to construct carbon-thiol bonds,carbon-sulfinic acid bonds,and carbon-disulfide bonds and such methodologies have been widely adopted by other research groups over multidisciplinary *** this article,our work on C-S bond formation in an aqueous solvent and its corresponding applications is summarized.

关键词： Green synthesis Biocompatible Water-based reaction Biologics C-S bond

Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides

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Chinese Chemical Letters 2021年第4期32卷 1411-1414页

作者： Rui-Hua Liu Qi-Chao Shan Ya Gao teck-peng loh Xu-Hong Hu Institute of Advanced Synthesis School of Chemistry and Molecular EngineeringNanjing Tech UniversityNanjing 211816China Division of Chemistry and Biological Chemistry School of Physical and Mathematical SciencesNanyang Technological UniversitySingapore 637371Singapore

Disclosed herein is an efficient Ag-catalyzed 4+1 heteroannulation reaction of enamides withα-carbonyl sulfoxonium *** diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline *** synthetic utility of the resultant tetrasubstituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.

关键词： Enamides Sulfoxonium ylides Oxazolines Silver catalysis Heteroannulation

Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes

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Chinese Journal of Chemistry 2019年第10期37卷 1036-1040页

作者： Shengjin Song Huan Liu Lu Wang Chuan Zhu teck-peng loh Chao Feng Department of Chemistry University of Science and Technology of ChinaHefeiAnhui 230026China Institute of Advanced Synthesis School of Chemistry and Molecular EngineeringJiangsu National Synergetic Innovation Center for Advanced MaterialsNanjing Tech UniversityNanjingJiangsu 211816China Division of Chemistry and Biological Chemistry School of Physical and Mathematical SciencesNanyang Technological University637371Singapore

Herein,we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)-C(sp2) cross-coupling of gem-difluoroalkenes and *** merging Rh(Ⅲ)-catalyzed C(sp2)-H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene,an efficient defluorinative vinylation reaction is uncovered,which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild *** mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.

关键词： diene catalyzed fluorine

Stereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidines via Copper-Catalyzed Cyclization of Alkenes

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Chinese Journal of Chemistry 2016年第11期34卷 1076-1080页

作者： Sai-Hu Cai Bing-Chao Da Jia-Hui Zhou Yun-He Xu teck-peng loh Department of Chemistry University of Science and Technology of China Hefei Anhui 230026 China DiVision of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 637371 Singapore

An efficient methodology for the stereoselective synthesis of cis-2,5-disubstituted pyrrolidines using copper catalyst was developed. The corresponding cis-2,5-disubstituted pyrrolidines could be obtained in reasonable yields and with good stereoselectivities in the presence of 4,4＇-di-tert-butyl-2,2＇-bipyridine as ligand and l-methyl-2-pyrrolidinone as solvent.

关键词： stereoselectivity pyrrolidines copper-catalyzed cyclization

Rencent Progress In The Total Synthesis Of Natural Products

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Rencent Progress In The Total Synthesis Of Natural Products

中国化学会第九届全国有机化学学术会议

作者： teck-peng loh Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Department of Chemistry University of Science and Technology of China

＜正＞One of the objectives in our group is to search for new synthetic methods and concepts through the total synthesis of natural *** this presentation,I will go through some of the methodologies and concepts develo...

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Stereoelectronic versus Steric Tuning in the Prins Cyclization Reaction:Synthesis of 2,6-trans Pyranyl Motifs

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Stereoelectronic versus Steric Tuning in the Prins Cyclizati...

氟化学与美好生活——中国化学会第十一届全国氟化学会议

作者： teck-peng loh Division of Chemistry and Biological Chemistry School of Physical and Mathematical SciencesNanyang Technological University

Previously,we demonstrated that -alkoxy tethered homoallylic alcohol can undergo Prins cyclization with various aldehydes to afford the 2,6-trans tetrahydropyrans, albeit with low selectivity(cisltrans=50/50).We believe that the carbonyl group has stabilized the of the *** forcing the carbonyl group to adopt the axial *** a consequence,it led to the 2,6-trans tetrahydropyrans. We found that removal of the 1.3-diaxialinteraction by using allenic alcohols instead of the homoallylic alcohols may lead to higher 2.6-trans selectivity.

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Biomimetic Cationic Polyene cyclization

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Biomimetic Cationic Polyene cyclization

中国化学会第28届学术年会

作者： teck-peng loh Department of Chemistry University of Science and Technology of China Division of Chemistry and Biological Chemistry School of Physical and Mathematical SciencesNanyang Technological University

＜正＞The biosynthetic cationic polyene cyclizations of acyclic precursors squalene and（3S）-2,3-oxidosqualene lead to a vast array of known tricyclic,tetracyclic and pentacyclic natural products.2 In particular,lanosterol is biosynthesized in a single,economical and effective step from （3S）-2,3-oxidosqualene by a single 83-kDa *** impressive part about this reaction is the ability

关键词： polyene acetal-initiated natural products aqueous media high enantioselectivies

Copper Catalyzed Highly Regioselective Silylcupration of Terminal Alkynes to Form α-Vinylsilanes

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Copper Catalyzed Highly Regioselective Silylcupration of Ter...

氟化学与美好生活——中国化学会第十一届全国氟化学会议

作者： teck-peng loh Division of Chemistry and Biological Chemistry School of Physical and Mathematical SciencesNanyang Technological University

＜正＞A highly regioselective synthesis of branched vinylsilanes through silicon-copper additions to terminal alkynes catalyzed by copper（Ⅰ）was developed using methanol as *** corresponding vinylsilanes were obtain...

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