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Achmatowicz Reaction

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Floris P. J. T. Rutjes – One of the best experts on this subject based on the ideXlab platform.

  • A Biocatalytic Aza-Achmatowicz Reaction
    ACS Catalysis, 2016
    Co-Authors: Elena Fernández-fueyo, Sabry H. H. Younes, Stefan Van Rootselaar, René W. M. Aben, Rokus Renirie, Ron Wever, Dirk Holtmann, Floris P. J. T. Rutjes, Frank Hollmann
    Abstract:

    A catalytic, enzyme-initiated (aza-) Achmatowicz Reaction is presented. The involvement of a robust vanadium-dependent peroxidase from Curvularia inaequalis allows the simple use of H2O2 and catalytic amounts of bromide.

  • the aza Achmatowicz Reaction facile entry into functionalized piperidinones
    ChemInform, 2015
    Co-Authors: Ferdi Van Der Pijl, Floris L. Van Delft, Floris P. J. T. Rutjes
    Abstract:

    Amongst the various conversions that are known to transform the furan moiety into other functional groups or heterocyclic rings, the Achmatowicz Reaction and the corresponding aza-modification stand out as broadly applicable oxidative rearrangements. Both Reactions are synthetically useful transformations resulting either in pyranone or piperidinone structures, containing ample synthetic opportunities for further functionalization. In this review, we will provide a literature overview of the aza-Achmatowicz Reaction, including application of the resulting piperidinones in the synthesis of biologically active compounds and natural products.

  • The Aza‐Achmatowicz Reaction: Facile Entry into Functionalized Piperidinones
    European Journal of Organic Chemistry, 2015
    Co-Authors: Ferdi Van Der Pijl, Floris L. Van Delft, Floris P. J. T. Rutjes
    Abstract:

    Amongst the various conversions that are known to transform the furan moiety into other functional groups or heterocyclic rings, the Achmatowicz Reaction and the corresponding aza-modification stand out as broadly applicable oxidative rearrangements. Both Reactions are synthetically useful transformations resulting either in pyranone or piperidinone structures, containing ample synthetic opportunities for further functionalization. In this review, we will provide a literature overview of the aza-Achmatowicz Reaction, including application of the resulting piperidinones in the synthesis of biologically active compounds and natural products.

Arun K. Ghosh – One of the best experts on this subject based on the ideXlab platform.

  • Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz Reaction
    Organic & biomolecular chemistry, 2018
    Co-Authors: Arun K. Ghosh, Hannah M. Simpson, Anne M. Veitschegger
    Abstract:

    Enantioselective syntheses of decytospolide A and decytospolide B are described here. The current synthesis highlights an Achmatowicz rearrangement of an optically active furanyl alcohol followed by reduction of the resulting dihydropyranone hemiacetal with BF3·OEt2 and Et3SiH to provide the saturated tetrahydropyranyl alcohol directly. This reduction was investigated with a variety of other Lewis acids. The synthesis also features Noyori asymmetric transfer hydrogenation and Friedel–Crafts acylation. Overall, the synthesis provides ready access to the natural products and may be useful in the preparation of bioactive derivatives.

  • Achmatowicz Reaction and its application in the syntheses of bioactive molecules
    RSC Advances, 2016
    Co-Authors: Arun K. Ghosh, Margherita Brindisi
    Abstract:

    Substituted pyranones and tetrahydropyrans are structural subunits of many bioactive natural products. Considerable effort is devoted toward the chemical synthesis of these natural products due to their therapeutic potential as well as low natural abundance. These embedded pyranones and tetrahydropyran structural motifs have been the subject of synthetic interest over the years. While there are methods available for the synthesis of these subunits, there are issues related to regio- and stereochemical outcomes, as well as versatility and compatibility of Reaction conditions and functional group tolerance. The Achmatowicz Reaction, an oxidative ring enlargement of a furyl alcohol, was developed in the 1970s. The Reaction provides a unique entry to a variety of pyranone derivatives from functionalized furanyl alcohols. These pyranones provide convenient access to substituted tetrahydropyran derivatives. This review outlines general approaches to the synthesis of tetrahydropyrans, covering general mechanistic aspects of the Achmatowicz Reaction or rearrangement with an overview of the reagents utilized for the Achmatowicz Reaction. The review then focuses on the synthesis of functionalized tetrahydropyrans and pyranones and their applications in the synthesis of natural products and medicinal agents.

  • Enantioselective syntheses of FR901464 and spliceostatin A: potent inhibitors of spliceosome.
    Organic letters, 2013
    Co-Authors: Arun K. Ghosh, Zhi-hua Chen
    Abstract:

    Enantioselective syntheses of FR901464 and spliceostatin A, potent spliceosome inhibitors, are described. The synthesis of FR901464 has been accomplished in a convergent manner in 10 linear steps (20 total steps). The A-tetrahydropyran ring was constructed from (R)-isopropylidene glyceraldehyde. The functionalized tetrahydropyran B-ring was synthesized utilizing a Corey-Bakshi-Shibata reduction, an Achmatowicz Reaction, and a stereoselective Michael addition as the key steps. Coupling of A- and B-ring fragments was accomplished via cross-metametathesis.

Masahiro Terada – One of the best experts on this subject based on the ideXlab platform.

  • Organocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan
    Journal of the American Chemical Society, 2004
    Co-Authors: Daisuke Uraguchi, Keiichi Sorimachi, Masahiro Terada
    Abstract:

    A new asymmetric entry of the 1,2-aza-Friedel−Crafts Reaction catalyzed by a chiral phosphoric acid is described. The present Reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz Reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral γ-butenolid.

  • organocatalytic asymmetric aza friedel crafts alkylation of furan
    Journal of the American Chemical Society, 2004
    Co-Authors: Daisuke Uraguchi, Keiichi Sorimachi, Masahiro Terada
    Abstract:

    A new asymmetric entry of the 1,2-aza-Friedel−Crafts Reaction catalyzed by a chiral phosphoric acid is described. The present Reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz Reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral γ-butenolid.

Ferdi Van Der Pijl – One of the best experts on this subject based on the ideXlab platform.

  • the aza Achmatowicz Reaction facile entry into functionalized piperidinones
    ChemInform, 2015
    Co-Authors: Ferdi Van Der Pijl, Floris L. Van Delft, Floris P. J. T. Rutjes
    Abstract:

    Amongst the various conversions that are known to transform the furan moiety into other functional groups or heterocyclic rings, the Achmatowicz Reaction and the corresponding aza-modification stand out as broadly applicable oxidative rearrangements. Both Reactions are synthetically useful transformations resulting either in pyranone or piperidinone structures, containing ample synthetic opportunities for further functionalization. In this review, we will provide a literature overview of the aza-Achmatowicz Reaction, including application of the resulting piperidinones in the synthesis of biologically active compounds and natural products.

  • The Aza‐Achmatowicz Reaction: Facile Entry into Functionalized Piperidinones
    European Journal of Organic Chemistry, 2015
    Co-Authors: Ferdi Van Der Pijl, Floris L. Van Delft, Floris P. J. T. Rutjes
    Abstract:

    Amongst the various conversions that are known to transform the furan moiety into other functional groups or heterocyclic rings, the Achmatowicz Reaction and the corresponding aza-modification stand out as broadly applicable oxidative rearrangements. Both Reactions are synthetically useful transformations resulting either in pyranone or piperidinone structures, containing ample synthetic opportunities for further functionalization. In this review, we will provide a literature overview of the aza-Achmatowicz Reaction, including application of the resulting piperidinones in the synthesis of biologically active compounds and natural products.

  • organocatalytic entry into 2 6 disubstituted aza Achmatowicz piperidinones application to sedacryptine and its epimer
    Organic Letters, 2014
    Co-Authors: Ferdi Van Der Pijl, Floris L. Van Delft, Robert K Harmel, Gaston J J Richelle, Peter Janssen, Floris P. J. T. Rutjes
    Abstract:

    Enantiomerically pure 2,6-disubstituted piperidinones were synthesized from furfural involving an organocatalyzed Mannich Reaction, aza-Achmatowicz Reaction, and an N-acyliminium ion-mediated coupling step. This approach was also successfully applied to a total synthesis of (−)-sedacryptine and one of its epimers.

Jan Deska – One of the best experts on this subject based on the ideXlab platform.

  • Chemoenzymatic Total Synthesis of (+)- & (−)-cis-Osmundalactone
    Journal of Molecular Catalysis B: Enzymatic, 2016
    Co-Authors: Fabian Blume, Daniel Thiel, Yu-chang Liu, Jan Deska
    Abstract:

    Both optical antipodes of the cis-isomers of osmundalactone, a hydroxypyranone natural product and core structure of the angiopterlactones, have been synthesized from acetylfuran in only three steps through a redox cascade utilizing oxidoreductases and transition metal catalysis in a concerted fashion. The key step in this fully catalytic strategy is the enzyme-mediated Achmatowicz Reaction via selective furan oxygenation to furnish the pyran core structure.

  • the Achmatowicz rearrangement oxidative ring expansion of furfuryl alcohols
    Synthesis, 2015
    Co-Authors: Daniel Thiel, Jan Deska, Eleonora Gianolio
    Abstract:

    Over the years, the oxidative ring enlargement of furfuryl alcohols, known as the Achmatowicz Reaction, has been developed into a powerful and versatile synthetic tool for the preparation of 6-hydroxypyranones. This review provides a comprehensive collection of the various ways to perform Achmatowicz rearrangement Reactions and explores the role of this ring-expansion process in contemporary organic synthesis. 1 Introduction 2 Classical Methods and Variants 3 Single-Electron-Transfer Oxidations 4 Metal-Catalyzed Ring Expansions 5 Photolytic Oxygenations 6 Enzymatic Transformations 7 Conclusions

  • Enzymatic aerobic ring rearrangement of optically active furylcarbinols
    Nature Communications, 2014
    Co-Authors: Daniel Thiel, Diana Doknić, Jan Deska
    Abstract:

    Biogenic furans are currently discussed as highly attractive alternative feedstock in a post-fossil society; thus, also the creation of sustainable furan valorization pathways appears of great importance. Here an artificial Achmatowicz monooxygenase activity for the aerobic ring expansion of furans is achieved by the combination of commercial glucose oxidase as oxygen-activating biocatalyst and wild-type chloroperoxidase as oxygen-transfer mediator, providing a biological ready-to-use solution for this truly synthetic furan rearrangement. In concert with enzymatic transformations for the enantioselective preparation of optically active furylcarbinols, purely biocatalytic Reaction cascades for the stereocontrolled construction of complex pyranones are obtained, exhibiting high functional group tolerance even to oxidation-sensitive moieties. The Achmatowicz Reaction involves the conversion of furans into dihydropyrans, classically with the use of bromine. Here, the authors couple an enzymatic oxygen activation with a chloroperoxidase-mediated oxygen transfer, providing a biocatalytic route to a formal Achmatowicz Reaction.