A5052874928- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Catalytic C–H Functionalization Methods
- Catalytic Cross-Coupling Reactions
- Asymmetric Synthesis and Catalysis
- Cyclopropane Reaction Mechanisms
- Synthesis of Indole Derivatives
- Sulfur-Based Synthesis Techniques
- Asymmetric Hydrogenation and Catalysis
- Synthesis and Catalytic Reactions
- Catalytic Alkyne Reactions
- Axial and Atropisomeric Chirality Synthesis
- Oxidative Organic Chemistry Reactions
- Chemical synthesis and alkaloids
- Synthesis and biological activity
- Chemical Synthesis and Reactions
- Bioactive Natural Diterpenoids Research
- Synthetic Organic Chemistry Methods
- Crystallography and molecular interactions
- Computational Drug Discovery Methods
- Natural product bioactivities and synthesis
- Click Chemistry and Applications
- Plant-based Medicinal Research
- Traditional and Medicinal Uses of Annonaceae
- Synthesis and Biological Evaluation
China Pharmaceutical University
2016-2025
State Key Laboratory of Natural Medicine
2017-2021
State Council of the People's Republic of China
2017
Nanjing Library
2014
Chinese Academy of Sciences
2009-2011
Shanghai Institute of Materia Medica
2011
In-Q-Tel
2009-2010
Shanghai Institute of Organic Chemistry
2009
A chiral thiourea catalyzed asymmetric 1,6-conjugate addition of para-quinone methides with dicyanoolefins has been developed. The reaction provided an efficient approach to the synthesis diarylmethine skeletons in good yields (up 99% yield) high diastereo- and enantioselectivity (>20:1 dr up 99.5:0.5 er), also on a gram scale. preliminary mechanistic study showed that remote stereocontrol was achieved through intermolecular hydrogen-bond interaction between catalyst directly for first time.
A novel [3 + 2] annulation between para-quinone methides and vinylcyclopropanes for the synthesis of spiro[4.5]deca-6,9-diene-8-ones has been described. The palladium phosphine-thiourea cooperative catalysis system played an important role in high yields diastereoselectivities. reaction exhibited good functional group tolerance scalability.
A formal 1,6-conjugated addition-mediated [2+1] annulation to synthesize spiro[2.5]octa-4,7-dien-6-one with p-quinone methides and sulfur ylides has been described. This domino-type process was highly diastereoselective exhibited good functional group tolerance scalability without the use of metals bases.
An efficient construction of fused indolines with a 2-quaternary center through palladium-catalyzed intramolecular Heck reaction N-(2(2-halobenzoxyl)-2,3-disubstituted indoles is disclosed. This protocol provided straightforward access to diverse good functional group tolerance.
A Rh(III)-catalyzed annulation between salicylaldehydes and diazo compounds with controllable chemoselectivity is described. AgNTf2 favored benzofurans via a tandem C–H activation/decarbonylation/annulation process, while AcOH led to chromones through activation/annulation pathway. The reaction exhibited good functional group tolerance scalability. Moreover, only single regioisomer of benzofuran was obtained due the in situ decarbonylation orientation effect.
Spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers was synthesized in one pot without the use of metals.
A series of novel quinoline–chalcone derivatives were designed, synthesized, and evaluated for their antiproliferative activity. Among them, compound 24d exhibited the most potent activity with IC50 values ranging from 0.009 to 0.016 μM in a panel cancer cell lines. Compound also displayed good safety profile an LD50 value 665.62 mg/kg by intravenous injection, its hydrochloride salt 24d-HCl significantly inhibited tumor growth H22 xenograft models without observable toxic effects, which was...
The cytotoxicity of the natural ent-kaurene diterpenoid, oridonin, has been extensively studied. However, application oridonin for cancer therapy was hampered primarily by its moderate potency. In this study, a series A-ring modified analogues, and their derivatives bearing various substituents on 14-OH position, were designed, synthesized, evaluated anticancer efficacy. Some significantly more potent than against both drug-sensitive drug-resistant cells. most compound, 13p, 200-fold...
Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, regioselectivity, obviating the need for oxidants, only environmentally benign N2 H2O were released. Further utilization method provided alternative route functionalized isoquinolines.
A 1,6‐addition arylation reaction of para ‐quinone methides with α‐isocyanoacetamides and electron‐rich aromatic compounds under metal‐free conditions has been developed. BF 3 · Et 2 O plays two roles in the reaction: catalyzing cyclization to give oxazoles, activating achieve process. The shows good functional group tolerance, scalability, regioselectivity. It is a consice protocol for synthesis diverse unsymmetrical triarylmethanes. Further transformation resulting triarylmethanes provides...
Ligand-controlled, palladium-catalyzed asymmetric [4+4] and [2+4] cycloaddition reactions of benzofuran-derived azadienes have been developed. Taking advantage chiral P,N-ligand (S,Rp)-PPFA, we obtained a variety benzofuro[2,3-c][1,5] oxazocines in good yields with excellent enantioselectivities via reactions. Employing P,P-ligand (S)-Cl-MeO-BIPHEP, the chemo- regioselectivities were switched to synthesize tetrahydropyran-fused spirocyclic compounds efficiency
Pd-catalyzed sequential hydroamination of readily available 1,3-enynes is reported. The redox-neutral process provides an efficient route to synthesize a broad scope imidazolidinones, thiadiazolidines, and imidazolidines. Asymmetric generates series synthetically valuable, enantioenriched imidazolidinones. Mechanistic studies revealed that the transformation occurred via intermolecular enyne pathway give allene intermediate. Subsequent intramolecular intermediate proceeded under...
Diaryl ethers are important structural motifs widely found in bioactive natural products, ligands, and catalysts. While there a variety of methods available to generate diaryl ethers, progress on the construction axially chiral has been slow. We report herein an atroposelective copper-catalyzed cycloaddition between bisalkynes azides. With indane-fused BOX ligand used, diverse array C–O atropisomers obtained with up 97% yield 99% ee. Control experiments showed that sequential...
A solvent-controlled switchable C–H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates via a Pd(OAc)2 catalyzed oxidative Heck reaction was first realized. The corresponding C2 and C5 products were obtained in good yields with high regioselectivities, respectively. selective C5-alkenylation successfully applied to the total synthesis (±)-rhazinilam.
2,3-Dihydrobenzofurans were achieved <italic>via</italic> a 1,6-conjugated addition-mediated [4 + 1] annulation of <italic>ortho</italic>-hydroxyphenyl-substituted <italic>para</italic>-quinone methides in high yields with diastereoselectivity.
A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series tetrahydro-β-carbolinones good yields under mild conditions. Gram-scale experiments further derivatization highlighted potential utility our method.
Abstract A regioselective synthesis of indole‐3‐carboxylic acid esters from anilines and diazo compounds has been realized by making use the pyrimidyl group‐assisted rhodium‐catalyzed CH activation CN bond formation. The reaction proceeds under mild conditions, exhibits good functional group tolerance scalability. Reutilization directing in resulting products provided an efficient strategy for further C‐7 functionalization indoles. Moreover, moiety could be readily removed as a leaving to...
A cascade three-component iodoazidation of para-quinone methides to construct spiro[4.5]deca-6,9-dien-8-ones under mild conditions has been developed. The chemoselective 1,6-addition azide radical triggered a regioselective 5-exo-dig cyclization/radical coupling sequence, enabling C-N, C-C, and C-I bond formations in one-pot procedure with high efficiency.
A novel [3 + 2] cycloaddition reaction between in situ formed azaoxyallyl cations and aldehydes has been developed. This concise method allows the rapid formation of a number oxazolidin-4-ones high yields with good functional group tolerance at room temperature. Further transformation late-stage modifications drug molecules could also be achieved yields, highlighting potential utility reaction.
Abstract A palladium‐catalyzed asymmetric reductive Heck reaction of unactivated aliphatic alkenes, with eliminable β‐hydrogen atoms, has been realized for the first time. series optically active bicyclo[3.2.1]octanes bearing chiral quaternary and tertiary carbon stereocenters were obtained in good yields excellent enantioselectivities, exhibiting functional‐group tolerance scalability. Moreover, deuterated also high efficiency.
A Rh(III)-catalyzed cascade annulation/C-H activation of o-ethynylanilines with diazo compounds has been developed. This concise method allows for the rapid formation a number benzo[a]carbazoles in high yields, exhibiting good functional group tolerance and scalability. The key to success this approach involves one C-N bond two C-C formation, an aryl-to-aryl 1,4-rhodium migration.