Organocatalytic Asymmetric Cycloaddition Reaction of Ketenes

Wang, Aie; Zhang, Jinlong

doi:10.6023/cjoc1103301

Cited by 4 publications

(2 citation statements)

References 8 publications

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“…[ 34 ] Unfortunately, injectable hydrogels usually have weak mechanical properties and poor stability, making them unable to withstand external forces, thus limiting their application in bone engineering. [ 36 ] To overcome these limitations, photocrosslinked hydrogels, [ 37 ] which usually initiate chain polymerization via free radicals or bioorthogonal click reactions to achieve in situ curing, have become attractive biomaterials. [ 37,38 ] Such photocrosslinked hydrogels have better physical characteristics due to the balance between injectability and mechanical strength.…”

Section: Introductionmentioning

confidence: 99%

“…[ 36 ] To overcome these limitations, photocrosslinked hydrogels, [ 37 ] which usually initiate chain polymerization via free radicals or bioorthogonal click reactions to achieve in situ curing, have become attractive biomaterials. [ 37,38 ] Such photocrosslinked hydrogels have better physical characteristics due to the balance between injectability and mechanical strength. [ 39 ] Therefore, combining photocrosslinked hydrogels and CuBGs to form a dual biophysical and biochemical signal regulation system may be a promising solution for the treatment of IBD.…”

Section: Introductionmentioning

confidence: 99%

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Dual Photo‐Enhanced Interpenetrating Network Hydrogel with Biophysical and Biochemical Signals for Infected Bone Defect Healing

Jian

Ying

et al. 2023

Adv Healthcare Materials

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The healing of infected bone defects (IBD) is a complex physiological process involving a series of spatially and temporally overlapping events, including pathogen clearance, immunological modulation, vascularization, and osteogenesis. Based on the theory that bone healing is regulated by both biochemical and biophysical signals, in this study, a copper doped bioglass (CuBGs)/methacryloyl‐modified gelatin nanoparticle (MA‐GNPs)/methacrylated silk fibroin (SilMA) hybrid hydrogel is developed to promote IBD healing. This hybrid hydrogel demonstrates a dual‐photocrosslinked interpenetrating network mechanism, wherein the photocrosslinked SilMA as the main network ensures structural integrity, and the photocrosslinked MA‐GNPs colloidal network increases strength and dissipates loading forces. In an IBD model, the hydrogel exhibits excellent biophysical characteristics, such as adhesion, adaptation to irregular defect shapes, and in situ physical reinforcement. At the same time, by sequentially releasing bioactive ions such as Cu2+, Ca2+, and Si2+ ions from CuBGs on demand, the hydrogel spatiotemporally coordinates antibacterial, immunomodulatory and bone remodeling events, efficiently removing infection and accelerating bone repair without the use of antibiotics or exogenous recombinant proteins. Therefore, the hybrid hydrogel can be used as a simple and effective method for the treatment of IBD.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Dual Photo‐Enhanced Interpenetrating Network Hydrogel with Biophysical and Biochemical Signals for Infected Bone Defect Healing

Jian

Ying

et al. 2023

Adv Healthcare Materials

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Asymmetric Total Synthesis of Shizukaol J, Trichloranoid C and Trishizukaol A

Wang

et al. 2022

Angewandte Chemie

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The asymmetric total synthesis of three lindenane sesquiterpenoid oligomers, shizukaol J, trichloranoid C and trishizukaol A, has been accomplished concisely in 15, 16 and 18 longest linear steps, respectively. The expeditious construction of molecular architectures was facilitated by Nelson's catalytic asymmetric ketene-aldehyde cycloaddition, a sequence of allylic alkylation/reduction/acidic cyclization to forge a lactone, and a double aldol condensation cascade to construct the 5/6 bicyclic system. Diastereoselective nucleophilic substitution promoted by a phase transfer catalyst constructed the C 11 quaternary stereogenic center, thus prompting synthetic efficacy toward shizukaol J. The synthesis of trichloranoid C and trishizukaol A was achieved after a cascade involving furanyl diene formation and a Diels-Alder reaction, as well as a one-pot sequence involving furan oxidation and global deprotection. Furthermore, our biological evaluation revealed that two compounds exhibited unexpected toxicity against tumor cell lines.

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Asymmetric Total Synthesis of Shizukaol J, Trichloranoid C and Trishizukaol A

Wang

et al. 2022

Angew Chem Int Ed

View full text Add to dashboard Cite

The asymmetric total synthesis of three lindenane sesquiterpenoid oligomers, shizukaol J, trichloranoid C and trishizukaol A, has been accomplished concisely in 15, 16 and 18 longest linear steps, respectively. The expeditious construction of molecular architectures was facilitated by Nelson's catalytic asymmetric ketene–aldehyde cycloaddition, a sequence of allylic alkylation/reduction/acidic cyclization to forge a lactone, and a double aldol condensation cascade to construct the 5/6 bicyclic system. Diastereoselective nucleophilic substitution promoted by a phase transfer catalyst constructed the C11 quaternary stereogenic center, thus prompting synthetic efficacy toward shizukaol J. The synthesis of trichloranoid C and trishizukaol A was achieved after a cascade involving furanyl diene formation and a Diels–Alder reaction, as well as a one‐pot sequence involving furan oxidation and global deprotection. Furthermore, our biological evaluation revealed that two compounds exhibited unexpected toxicity against tumor cell lines.

show abstract

Organocatalytic Asymmetric Cycloaddition Reaction of Ketenes

Cited by 4 publications

References 8 publications

Dual Photo‐Enhanced Interpenetrating Network Hydrogel with Biophysical and Biochemical Signals for Infected Bone Defect Healing

Dual Photo‐Enhanced Interpenetrating Network Hydrogel with Biophysical and Biochemical Signals for Infected Bone Defect Healing

Asymmetric Total Synthesis of Shizukaol J, Trichloranoid C and Trishizukaol A

Asymmetric Total Synthesis of Shizukaol J, Trichloranoid C and Trishizukaol A

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