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Discovery and application of 6π-azaelectrocyclization to natural product synthesis and synthetic biology

Science China Chemistry 2012年第1期55卷 19-30页

作者： TANAKA Katsunori KATSUMURA Shigeo FUKASE Koichi Department of Chemistry Graduate School of ScienceOsaka University1-1 Machikaneyama Department of Chemistry and Open Research Center on Organic Tool Molecules School of Science and TechnologyKwansei Gakuin University

While elucidating the inhibitory mechanism of a hydrolytic enzyme by aldehyde-containing natural product,we discovered a reaction involving a rapid 6π-azaelectrocyclization of azatrienes generated from aldehyde with lysine *** electrocyclic reaction of the 1-azatriene system,a cyclization precursor,exhibited a significant substituent *** chiral piperidine synthesis and a one-pot library synthesis of pyridines on solid-supports were applied to synthesize pyridine/indole alkaloid-type natural ***,we developed lysine-based labeling and engineering of biomolecules and living cells based on the rapid 6π-*** labels and oligosaccharide structures were introduced efficiently and selectively into surface lysines under the mild conditions;notable effects of N-glycans on proteins and living cells were visualized for the first time by PET and noninvasive fluorescence imaging.

关键词： 6π-azaelectrocyclization enzyme inhibition lysine natural product synthesis synthetic biology labeling chemical engineering living cells N-glycan in vivo imaging tumor targeting

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Asymmetric catalytic hydrogenation of imines and enamines in natural product synthesis

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Green synthesis and Catalysis 2020年第1期1卷 26-41页

作者： Pei Tang Huijing Wang Wen Zhang Fen-Er Chen Sichuan Research Center for Drug Precision Industrial Technology West China School of PharmacySichuan UniversityChengdu 610041China Engineering Center of Catalysis and synthesis for Chiral Molecules Department of ChemistryFudan UniversityShanghai 200433China Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs Shanghai 200433China

Asymmetric catalytic hydrogenations of imines and enamines with chiral transition-metal complexes bearing chiral ligands are among the most green and powerful approaches for the elaboration of chiral amine structures in organic *** review focuses on recent applications of asymmetric hydrogenations of imine and enamine substrates in the total syntheses of natural *** applications include diverse processes involving asymmetric transfer hydrogenation(ATH)and asymmetric hydrogenation(AH)to form key chiral amine motifs in natural products with good efficiency and high-level enantiocontrol.

关键词： Asymmetric catalytic hydrogenation Imine substrates Enamine substrates natural product synthesis Enantioselectivity

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Enantioselective iridium-catalyzed allylic substitution with a Reformatsky reagent: direct construction of β-stereogenic homoallylic esters

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Science China Chemistry 2024年第11期67卷 3791-3797页

作者： Debasis Pal Kirana DVeeranna Yuk Fai Wong PAndrew Evans Department of Chemistry Queen’s University90 Bader LaneKingstonK7L 3N6Canada Xiangya School of Pharmaceutical Sciences Central South UniversityChangsha410013China

The Reformatsky reagent derived from ethyl bromoacetate circumvents the challenge associated with the direct regio-and enantioselective iridium-catalyzed allylic alkylation with an unstabilized aliphatic ester enolate. Notably, this work represents the first example of using a Reformatsky reagent in a metal-allyl reaction, which permits the direct construction of enantioenriched β-stereogenic homoallylic esters without preactivation of the pronucleophile or post-reaction modification of the product(e.g., thermal decarboxylation of a 1,3-dicarbonyl). Moreover, the process allows the coupling of a broad range of sterically and electronically diverse electrophiles bearing aryl, heteroaryl and alkenyl derivatives, including the significantly more challenging alkyl-substituted allylic carbonates. The versatility of the ester product is exemplified by a series of functional group manipulations and the development of a concise and efficient enantioselective total synthesis of the natural product,(+)-descurainolide A. Finally, mechanistic studies indicate that the zinc enolate behaves as a soft nucleophile that undergoes outer-sphere alkylation.

关键词： allylic substitution asymmetric catalysis mechanistic studies natural product synthesis Reformatsky reagent

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Dinitrogen extrusion from diazene in organic synthesis

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Chinese Chemical Letters 2022年第8期33卷 3695-3700页

作者： Chunngai Hui Shiping Wang Chunfa Xu Institute of Pharmaceutical Science and Technology College of ChemistryFuzhou UniversityFuzhou 350108China National Engineering Research Center of Chemical Fertilizer Catalyst College of Chemical EngineeringFuzhou UniversityFuzhou 350108China Max Planck Institute of Molecular Physiology Department of Chemical BiologyDortmund 44227Germany

Radical-mediated reactions have many advantages in the construction of complex molecular scaffolds by forging chemical bonds of high ***,including 1,1-diazenes and 1,2-diazenes,can generate biradical species via nitrogen extrusion under thermal or photochemical *** superior reactivity of the generated biradical enables various types of synthetic transformations with excellent chemoselectivity and has been applied to the complex natural products *** this mini-review,the modes of reaction are summarized and discussed,namely ring contraction via nitrogen deletion,homo or heterodimerization,trimethylenemethane(TMM)-diyl *** of these classes of reactions in complex natural product synthesis are *** but not least,the current state,future directions,and opportunities for dinitrogen extrusion reaction from diazenes are highlighted and discussed.

关键词： Diazene Biradical Dimerization Ring contraction natural product synthesis

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Unification of Anion Relay Chemistry(ARC) with the Takeda and Hiyama/Denmark Cross-Coupling Reactions:Identification of an Effective Silicon-Based Transfer Agent

Unification of Anion Relay Chemistry(ARC) with the Takeda an...

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化学使世界更美好——中国化学会第七届有机化学学术会议

作者： Amos B.Smith Ⅲ Department of Chemistry Penn Center for Molecular Discovery and the Monell Chemical Senses CenterUniversity of PennsylvaniaPhiladelphiaPA19123

Anion Relay Chemistry(ARC),an effective multi-component union protocol,recently developed and employed in our laboratory,holds great potential for chemists requiring rapid increase of molecular complexity in a single operation,with precise control of stereogenicity on route to both natural and "natural product-like" targets for biomedical research. Employing this technique,a large number of diverse structures can be assembled rapidly from a small number of initiating nucleophiles,bifunctional linchpins,and electrophiles in a controlled,multi-component coupling *** to expand the scope of this tactic include the construction of natural products, as well as libraries of "natural product-like" compounds, which highlight the robust nature of this *** of the ARC tactic,involving both TypeⅠand TypeⅡprotocols,will be presented with illustrations arising from alkaloid and polyketide/macrolide total synthetic ventures currently ongoing in our *** addition,observations regarding the intersection of the ARC TypeⅡprotocol with previously reported reaction pathways, notably in the area of Pd-mediated Takeda and Hiyama/Denmark cross-coupling reactions,will be presented.

关键词： Anion Relay Chemistry natural product synthesis Diversity-Oriented synthesis Brook Rearrangement Cross-Coupling

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