The synthesis of 1-pyrrolines from cyclobutanol derivatives and an aminating reagent (MsONHOTf) has been developed. This one-pot procedure achieves C-N bond/C═N bond formation via ring expansion. A series of 1-pyrroline derivatives are synthesized in moderate to good yields under mild conditions.
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http://dx.doi.org/10.1021/acs.orglett.1c04304 | DOI Listing |
RSC Med Chem
January 2025
School of Chemical Sciences, University of Auckland Auckland 1010 New Zealand
Dysregulation of choline phospholipid metabolism and overexpression of phosphatidylcholine-specific phospholipase C (PC-PLC) is implicated in various cancers. Current known enzyme inhibitors include compounds based on a 2-morpholino-5--benzylamino benzoic acid, or hydroxamic acid, scaffold. In this work, 81 compounds were made by modifying this core structure to explore the pharmacophore.
View Article and Find Full Text PDFNat Geosci
December 2024
Université Paris Cité, Institut de Physique du Globe de Paris, CNRS, Paris, France.
Saturn's rings have been estimated to be as young as about 100 to 400 million years old according to the hypothesis that non-icy micrometeoroid bombardment acts to darken the rings over time and the Cassini observation indicated that the ring particles appear to be relatively clean. These young age estimates assume that the rings formed out of pure water ice particles with a high accretion efficiency of impacting non-icy micrometeoroid material ( ≳ 10%). Here we show, using numerical simulations of hypervelocity micrometeoroid impacts on a ring particle, that non-icy material may not be as readily accreted as previously thought.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Laboratory of Synthesis and Natural Products (LSPN), Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, CH-1015 Lausanne, Switzerland.
In the dyotropic rearrangement of molecules with semiflexible structures, characterized by a freely rotating static C-C bond, the formation of a mixture of products is common due to the coexistence of several energetically comparable conformers. Herein, we report that it is possible to modulate the shifting groups by adjusting the metal's coordination sphere in Pd-based dyotropic rearrangement. In the presence of a catalytic amount of Pd(II) salt, the reaction of γ-hydroxyalkenes or γ,δ-dihydroxyalkenes with Selectfluor affords fluorinated tetrahydropyranols or 6,8-dioxabicyclo[3.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Enamine Ltd, Organic synthesis for drug discovery, UKRAINE.
A general method to convert simple exocyclic alkenes (no Ar-substituents) into saturated F2-rings has been developed. The reaction involves the IIII-reagent C6F5I(OAc)2 (F5-PIDA). The reaction efficiently works on the mg-, g-, and even multigram scale.
View Article and Find Full Text PDFChemistry
January 2025
The University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, M1 7DN, Manchester, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
The natural product synthesis of brevione J undergoes a cascade of reactions including an oxidative desaturation and a ring-expansion. The C1-C2 desaturation of brevione B is catalyzed by the nonheme iron dioxygenase BrvJ using one molecule of O2 and a-ketoglutarate (aKG). However, whether the subsequent oxidative ring expansion reaction is also catalyzed by the same enzyme is unknown and remains controversial.
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