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Total Syntheses of Nominal and Actual Prorocentin.
J Am Chem Soc
February 2023
Max-Planck-Institut für Kohlenforschung, 45478 Mülheim/Ruhr, Germany.
The dinoflagellate-derived polyether prorocentin is a co-metabolite of the archetypical serine/threonine phosphatase inhibitor okadaic acid. Whereas a structural relationship cannot be missed and a biosynthetic link was proposed, it is currently unknown whether there is any parallel in the bioactivity profile of these natural products. However, it was insinuated in the past that the structure assigned to prorocentin might need to be revised.
View Article and Find Full Text PDFCyclic Hypervalent Iodine Reagents: Enabling Tools for Bond Disconnection via Reactivity Umpolung.
Acc Chem Res
December 2018
Laboratory of Catalysis and Organic Synthesis , Ecole Polytechnique Fédérale de Lausanne , EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne , Switzerland.
The efficient synthesis of organic compounds is an important field of research, which sets the basis for numerous applications in medicine or materials science. Based on the polarity induced by functional groups, logical bond disconnections can be deduced for the elaboration of organic compounds. Nevertheless, this classical approach makes synthesis rigid, as not all bond disconnections are possible.
View Article and Find Full Text PDFScope and Mechanism of Cooperativity at the Intersection of Organometallic and Supramolecular Catalysis.
J Am Chem Soc
August 2016
Chemical Sciences Division, Lawrence Berkeley National Laboratory and Department of Chemistry, University of California, Berkeley, California 94720, United States.
The scope and mechanism of the microenvironment-catalyzed C(sp(3))-C(sp(3)) reductive elimination from transition metal complexes [Au(III), Pt(IV)] is explored. Experiments detailing the effect of structural perturbation of neutral and anionic spectator ligands, reactive alkyl ligands, solvent, and catalyst structure are disclosed. Indirect evidence for a coordinatively unsaturated encapsulated cationic intermediate is garnered via observation of several inactive donor-arrested inclusion complexes, including a crystallographically characterized encapsulated Au(III) cation.
View Article and Find Full Text PDFGold- and platinum-catalyzed formal Markownikoff's double hydroamination of alkynes: a rapid access to tetrahydroquinazolinones and angularly-fused analogues thereof.
J Org Chem
February 2010
Organic Chemistry Division II, Indian Institute of Chemical Technology, Hyderabad 500 607, India.
A highly efficient gold(I)- and platinum(II)-catalyzed process for formal Markownikoff's double hydroamination of alkynes tethered with hydroxyl group has been developed. The method was shown to be applicable to a broad range of 2-aminobenzamides and alkynols leading to the formation of multiply substituted tetrahydroquinazolinones. Interestingly, when Pt(IV)Cl(4) catalyst was employed, cyclic angularly fused compound was obtained.
View Article and Find Full Text PDFGold- or platinum-catalyzed synthesis of sulfur heterocycles: access to sulfur ylides without using sacrificial functionality.
Angew Chem Int Ed Engl
February 2010
School of Chemistry, University of Birmingham, Edgbaston, B15 2TT, Birmingham, UK.
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