Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Arene isomerization can simultaneously edit the arene backbone and its periphery, thereby bridging the independent chemistry of two distinct arenes. Herein, a facile pyrone isomerization approach for the divergent synthesis of five- and sixfold-substituted biaryl phenols is achieved by using a relay Claisen rearrangement as a crucial step. This catalyst-free isomerization reaction features high step, atom, and redox economy by transferring the innate oxidation state of pyrone into the biaryl phenols. Additionally, an intriguing self-activation phenomenon was observed, which enabled the selective dienone-phenol rearrangement of the aryl group.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.5c01077 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Regioselectivity Switching in the Tandem Reaction of Skipped Diynones with Allylic Alcohols: Stereoselective Synthesis of 4-Allyl-2-Methylene-3(2)-Furanones.
J Org Chem
August 2025
A. E. Favorsky Irkutsk Institute of Chemistry SB RAS, 1 Favorsky St, Irkutsk, 664033, Russian Federation.
A novel base-catalyzed synthesis of hitherto unknown 4-allyl-2-methylene-3(2)-furanones from skipped diynones and allylic alcohols via nucleophilic addition/Claisen rearrangement/cyclization reaction is described. An important role of the employed catalytic system for the regioselective switching in the cyclization step from 3-allyl-4-pyrones to isomeric 4-allyl-3(2)-furanones is discussed. The isolation of main intermediates of the tandem reaction and study of their reactivity allowed us to develop a convenient two-stage protocol for stereoselective 4-allyl-2-methylene-3(2)-furanone formation featuring a good substrate tolerance and good yields of target products.
View Article and Find Full Text PDF(±)-Talapyrones A-F: six pairs of dimeric polyketide enantiomers with unusual 6/6/6 and 6/6/6/5 ring systems from Talaromycesadpressus.
Chin J Nat Med
August 2025
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address:
(±)-Talapyrones A-F (1-6), six pairs of dimeric polyketide enantiomers featuring unusual 6/6/6 and 6/6/6/5 ring systems, were isolated from the fungus Talaromyces adpressus. Their structures were determined by spectroscopic analysis and HR-ESI-MS data, and their absolute configurations were elucidated using a modified Mosher's method and electronic circular dichroism (ECD) calculations. (±)-Talapyrones A-F (1-6) possess a 6/6/6 tricyclic skeleton, presumably formed through a Michael addition reaction between one molecule of α-pyrone derivative and one molecule of C poly-β-keto chain.
View Article and Find Full Text PDFPyrone Isomerization Enabled Divergent Access to Multisubstituted Biaryl Phenol via Relay Claisen Rearrangement.
Org Lett
May 2025
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China.
Arene isomerization can simultaneously edit the arene backbone and its periphery, thereby bridging the independent chemistry of two distinct arenes. Herein, a facile pyrone isomerization approach for the divergent synthesis of five- and sixfold-substituted biaryl phenols is achieved by using a relay Claisen rearrangement as a crucial step. This catalyst-free isomerization reaction features high step, atom, and redox economy by transferring the innate oxidation state of pyrone into the biaryl phenols.
View Article and Find Full Text PDFTotal Synthesis and Stereochemical Assignment of Alternapyrone.
Molecules
April 2025
State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Alternapyrone, a bioactive polyketide produced by the fungal host , is biosynthesized by a polyketide synthase encoded by the gene cluster. Despite its known bioactivity, the stereochemical configuration of the three stereogenic centers in its polyketide backbone has remained unresolved. In this study, we determined the complete stereostructure of alternapyrone using an integrative approach that combines predictive, rule-based stereochemical analysis with experimental validation through total synthesis.
View Article and Find Full Text PDFMonolithic capillary electrochromatographic enantioseparation system for dichlorprop based on a novel nanomaterial synthesized by chiral metal organic frameworks and racemic-templated chiral molecular imprinted polymers.
Talanta
November 2025
Key Laboratory of Drug Quality Control and Pharmacovigilance (Ministry of Education), China Pharmaceutical University, Nanjing, 210009, PR China; State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, PR China. Electronic address:
Dichlorprop (DCPP), a chlorophenoxy herbicide with two enantiomers, shows distinct biological and toxicological properties: R-DCPP is highly effective as a herbicide, while S-DCPP lacks herbicidal activity and is toxic to non-target organisms. Efficient enantioseparation methods for DCPP are crucial for precise herbicide use, reduced agrochemical consumption, and minimized environmental impact. To achieve this purpose, a novel capillary monolithic column (L-His-ZIF-8@CMIP(rac-DCPP/PG-EDMA)@capillary) was fabricated using the nanomaterials synthesized by chiral molecularly imprinted polymers (CMIPs) and chiral metal-organic frameworks (CMOFs, L-His-ZIF-8) as stationary phases.
View Article and Find Full Text PDF