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8 results on '"Shugao Zhu"'

1. Synthesis of benzooxepane-fused cyclobutene derivatives via Pd-catalyzed cascade reactions of haloarenes and diynylic ethers.

Author

Shugao Zhu, Wenliang Huang, Shihan Liu, Rongjing Yu, Yufeng Ma, Hong Wang, Rui Zhang, Bin Liu, Yu Lan, and Ruwei Shen

Subjects
*ARYL halides, *ETHERS, *ISOMERIZATION, *RING formation (Chemistry)
Abstract

A tandem palladium-catalyzed Sonogashira coupling, propargyl-allenyl isomerization, and [2+2] cycloaddition sequence between electrondeficient haloarenes and 1,8-diynylic ethers is developed. The reaction shows good functional tolerance and proceeds under mild conditions to provide a new profile of benzooxepane-fused cyclobutene derivatives in moderate to high yields with high selectivity. The reaction mechanism is validated both by experimental studies and DFT calculations. [ABSTRACT FROM AUTHOR]

Published
2024
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2. Expanding peptide-cucurbit[7]uril interactions through selective N-terminal reductive alkylation

Author

Rolande Meudom, Danny Hung-Chieh Chou, Shugao Zhu, Michael T. Jacobsen, Liping Cao, and Nan Zheng

Subjects
chemistry.chemical_classification, Stereochemistry, Human calcitonin, Peptide, Sugar-dependent binding, QD415-436, Alkylation, Reductive alkylation, Biochemistry, chemistry, Terminal (electronics), Cucurbit[7]uril, pH-dependent binding, Pharmacology (medical), Peptides
Abstract

Cucurbit[7]uril (CB[7]) is a supramolecular binding host for peptides and proteins with N-terminal Phe. However, the low occurrence of such peptides and proteins limits broader applications of this unique host-guest interaction. Here, we report a strategy to expand the scope of CB[7]-peptide interaction by site-specifically introducing N-terminal substitutions (e.g. benzyl groups) using reductive alkylation. N-terminal benzylated peptides have similar affinity to CB[7] as native peptides with N-terminal Phe and even stronger interactions can be achieved using better ligands. We further expanded this host-guest interaction to be stimuli responsive. By introducing benzyl carboxylate substituents, the CB[7]-peptide interaction shows pH-dependent binding. Furthermore, benzyl boronate substituents led to saccharide-dependent CB[7]-peptide interactions. We demonstrated that using this strategy to introduce stronger CB[7] binders to the N-terminus of human calcitonin (hCT) results in increased aggregation stability in the presence of CB[7]. This strategy to expand CB[7]-peptide interaction scope opens opportunities for future applications in peptides and proteins.

Published
2022

3. Unexpected Pd-catalyzed coupling, propargyl-allenyl isomerization and Alder-ene reaction: facile synthesis of some not readily available 2,3-dihydrofuran derivatives

Author

Ruwei Shen, Shugao Zhu, and Xian Huang

Subjects
Aromatic compounds -- Chemical properties, Aromatic compounds -- Structure, Isomerization -- Usage, Palladium catalysts -- Chemical properties, Palladium catalysts -- Structure, Ethers -- Chemical properties, Ethers -- Structure, Biological sciences, Chemistry
Published
2009

5. Asymmetric Total Syntheses of Aspidodasycarpine, Lonicerine, and the Proposed Structure of Lanciferine.

Author

Yong Li, Shugao Zhu, Jian Li, and Ang Li

Subjects
*PLANT metabolites, *MICROBIAL metabolites, *ALKALOIDS, *HYDROGENATION, *ADDITION reactions, *GREEN diesel fuels, *CHEMICAL reactions, *CONDENSATION reactions
Abstract

Aspidodasycarpine and lonicerine are a pair of epimeric aspidophylline-type alkaloids bearing vicinal quaternary C7 and C16. The first and enantioselective total syntheses of these molecules are described here. A Ru-catalyzed asymmetric transfer hydrogenation established the first stereocenter. An Au-promoted Toste cyclization was exploited to assemble the bridged tetracyclic core and define the geometry of the exocyclic olefin; electron deficient (p-CF3C6H4)3P was a suitable ligand for this transformation. An aldol condensation followed by an intramolecular indole C3 alkylation constructed the adjacent quaternary C7 and C16 diastereoselectively, leading to a pentacyclic lactol as an advanced common intermediate for synthesizing both alkaloids. The proposed structure of lanciferine, a highly oxidized congener of aspidodasycarpine, was synthesized from the lactol by tuning the oxidation states of various carbons. [ABSTRACT FROM AUTHOR]

Published
2016
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7. Gold-Catalyzed Cyclization of 3-(2'-Azidoaryl)-1-arylpropargyl Carbonates or 3-Aryl-1-(2'-azidoaryl)propargyl Carbonates to Produce Quinolines.

Author

Shugao Zhu, Luling Wu, and Xian Huang

Subjects
*NUCLEOTIDE sequence, *CARBONATES, *GOLD catalysts, *QUINOLINE, *RING formation (Chemistry)
Abstract

A gold-catalyzed cyclization of 3-(2'-azidoaryl)-1-arylpropargyl carbonates to generate substituted quinolines via a sequence of 3,3-rearrangement, 6-endo-trig cyclization and denitrogenation has been developed. Similar products could be obtained from 3-aryl-1-(2'-azidoaryl)propargyl carbonates under different gold catalytic conditions via a sequential 6-endo-dig cyclization, denitrogenation, and 1,2-H shift process. [ABSTRACT FROM AUTHOR]

Published
2013
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8. Synthesis of Polycyclic Isoindoline Derivatives via Tandem Pd-Catalyzed Coupling, Propargyl--llenyl Isomerization, [4 + 2] Cycloaddition and Aromatization Reaction.

Author

Shugao Zhu, Jian Cao, Luling Wu, and Xian Huang

Subjects
*ISOMERIZATION, *CHEMICAL synthesis, *INDOLINE, *SONOGASHIRA reaction, *RING formation (Chemistry), *AROMATIZATION
Abstract

We report in this paper an interesting sequential reaction involving sequential Sonogashira coupling, propargyl-allenyl isomerization, [4 + 2] cycloaddition and aromatization reaction, which provides a facile method for the synthesis of a variety of polycyclic isoindoline derivatives from easily accessible starting materials. [ABSTRACT FROM AUTHOR]

Published
2012
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