98%
921
2 minutes
20
The concept of combining asymmetric aminocatalysis with electrochemistry remains underexplored. Herein, we report an electrochemically driven Diels-Alder cycloaddition reaction of substituted hydroquinones with a series of enals activated by a TMS-protected prolinol catalyst, leading to optically active products with high yields and perfect enantiomeric ratios up to 99 : 1 e.r.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/d5cc00505a | DOI Listing |
J Org Chem
September 2025
Pharmaron Drug Discovery Services Europe, Pharmaron UK Ltd., West Hill Innovation Park, Hertford Road, Hoddesdon EN11 9FH, United Kingdom.
Sulfur(VI) fluoride exchange (SuFEx) compounds are gaining increasing attention due to their various applications. We present the Diels-Alder reaction of ethenesulfonyl fluoride and analogues to rapidly access cyclic and bicyclic SuFEx derivatives in moderate to good yields. These derivatives have been shown to be useful intermediates in a variety of synthetic transformations to expand the toolkit for the preparation of cyclic aliphatic sulfonyl fluorides.
View Article and Find Full Text PDFNat Prod Bioprospect
September 2025
College of Pharmaceutical Sciences, Key Laboratory of Medicinal Chemistry and Molecular Diagnostics of Education Ministry of China, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei University, Baoding, 071002, People's Republic of China.
Five new heterodimers, chalasoergodimers A-E (1-5), and three known heterodimers (6-8), along with four chaetoglobosin monomers (9-12), were isolated from a marine-derived Chaetomium sp. fungus. The structures of new compounds 1-5 were elucidated by HRESIMS, NMR, chemical calculated C NMR and ECD methods.
View Article and Find Full Text PDFACS Chem Biol
September 2025
Institute for Biomedicine and Glycomics, Griffith University, Queensland, 4111 Brisbane, Australia.
Small-molecule metabolic chemical probes are tailored chemical biology tools that are designed to detect and visualize biological processes within a cell or an organism. Nucleoside analogues are a subset of metabolic probes that enable the study of DNA synthesis, proliferation kinetics, and cell cycle progression. However, most available nucleoside analogue probes have been designed for use in mammalian cells, limiting their use in other species, where there are metabolic pathway differences.
View Article and Find Full Text PDFTetrahedron
June 2025
Department of Chemistry, Vanderbilt University, 7330 Stevenson Center, Nashville, Tennessee 37235, United States.
Yaretol is a polycyclic norditerpene constituting a structurally distinct class of terpene natural products isolated from which, to date, has not been accessed via total synthesis. Herein, we report our synthetic efforts toward a key intramolecular Diels-Alder furan (IMDAF) cycloaddition to construct the carbon framework. We discuss our efforts toward the cycloaddition wherein undesired aromatization and unanticipated rearrangement of the cycloadduct are observed.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2025
Department of Chemistry, Fudan University, 220 Handan Rd, Shanghai, 200433, China.
The Diels-Alder/cheletropic retro-[4+1] cycloadditions of thiophene S,S-dioxides are a prominent method for synthesizing unsaturated six-membered carbocycles. However, to the best of our knowledge, catalytic asymmetric variations of these reactions have not yet been achieved. Herein, we report Fe(III)-bis(oxazoline) complex-catalyzed inverse-electron-demand [4+2] cycloaddition/cheletropic retro-[4+1] extrusion of SO reactions between thiophene S,S-dioxides and 3-substituted indoles.
View Article and Find Full Text PDF