The alkyl chain in the backbone of sphingosine derivatives can be exchanged with functionalised (labelled) side chains in a single step under cross-metathesis reaction conditions.
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http://dx.doi.org/10.1039/b508132g | DOI Listing |
J Nat Prod
December 2024
Department of Chemistry, University of Kalyani, Kalyani 741235 West Bengal, India.
A concise synthetic route to an epimer of the recently isolated biologically active cyclic tetrapeptide koshidacin B has been developed, which featured a late-stage functionalization of a macrocyclic scaffold through a cross metathesis reaction. The synthetic 9--koshidacin B showed marginal differences in spectroscopic behavior with that of the natural product but exhibited conformational preferences similar to those reported for analogous substrate chlamydocin. Moreover, it exhibited a useful level of selective inhibition of biologically relevant enzyme histone deacetylase 1 with an IC value of 0.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, ETH Zurich, Zurich 8093, Switzerland.
Methyltrioxorhenium (MTO) supported on AlO or SiO-AlO is an efficient heterogeneous alkene metathesis catalyst that works at room temperature and tolerates various functional groups. Surface studies found that MTO interacts with highly Lewis-acidic aluminum centers and that its methyl group is probably C-H activated resulting in rhenium-methylidene species. The exact structure of the catalyst resting state and the active species is subject to scientific debate.
View Article and Find Full Text PDFChemistry
November 2024
Faculty of Natural Science II, Institute of Chemistry, Macromolecular Chemistry, Martin Luther University Halle-Wittenberg, von-Danckelmann-Platz 4, Halle/Saale, D-06120, Germany.
The molecular environment around supramolecular bonding systems significantly affects their stability and the assembly of host-guest complexes, most prominent for hydrogen bonds (H-bonds). Hamilton receptor-barbiturate host-guest complexes are well-known in solution, typically forming a 1 : 1 molar ratio complex. However, within a polymer matrix, these complexes can form higher-order assemblies, deviating from the standard 1 : 1 complex, which are challenging to characterize and often require lab-intensive methods.
View Article and Find Full Text PDFTransition metal-catalyzed alkyne metathesis has become a useful tool in synthetic chemistry. Well-defined alkyne metathesis catalysts comprise alkylidyne complexes of tungsten, molybdenum and rhenium. Non-d Re(v) alkylidyne catalysts exhibit advantages such as remarkable tolerance to air and moisture as well as excellent functional group compatibility.
View Article and Find Full Text PDFCarbohydr Res
November 2024
Instituto de Ciencias Básicas, Universidad Veracruzana, Luis Castelazo Ayala, Col. Industrial Ánimas, CP 91190, Xalapa, Ver., Mexico. Electronic address:
A stereoselective synthesis of fused tricyclic framework of epi-parvistemonine A from D-glucono-δ-lactone is described. The synthetic strategic is based on the stereoselective construction of the 7-membered cyclic skeleton via a cross-metathesis reaction followed by a Michael type cyclization promoted by TfO.
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