Benjamin D. A. Shennan

Lactam Framework Editing via Formal Methylene Deletion

Nicholas D’Arcy-Evans, Gabriele Rossini, Benjamin D. A. Shennan, Darren J. Dixon

High Resolution Image Download MS PowerPoint Slide Lactams are cyclic amide building blocks of fundamental importance within synthetic chemistry and drug discovery. Despite their ubiquity, general and convenient methods to interconvert between ring sizes are scarce. Herein, we disclose a new and …

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Synthesis of the Tetracyclic Core of the Daphlongeranines

Benjamin D. A. Shennan, P. W. Smith, Yusuke Ogura, E.A. Kallstrom et autres

High Resolution Image Download MS PowerPoint Slide The first synthesis of the tetracyclic core of the daphlongeranine natural product family is reported. Containing a tricyclic core unique to this subfamily of the Daphniphyllum alkaloids and featuring two quaternary carbons, this 11-step synthetic …

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Catalytic Phosphorylation of Tyrosine via a Radical Arbuzov Reaction

Benjamin D. A. Shennan, T Fukuta, Mina Yamane, Takashi Koyama et autres

Synthetic protein/peptide modification is a powerful strategy for the development of new therapeutics and tools for chemical biology. Accordingly, the development of a synthetic variant of biological tyrosine phosphorylation, a cornerstone of the post-translational modification landscape, could find widespread application in the …

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Catalytic Phosphorylation of Tyrosine via a Radical Arbuzov Reaction

Benjamin D. A. Shennan, T Fukuta, Mina Yamane, Takeshi Koyama et autres

Synthetic protein/peptide modification is a powerful strategy for the development of new therapeutics and tools for chemical biology. Accordingly, the development of a synthetic variant of biological tyrosine phosphorylation, a cornerstone of the post-translational modification landscape, could find widespread application in the …

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CCDC 2296864: Experimental Crystal Structure Determination

Anna A. M. Miller, Phillip Biallas, Benjamin D. A. Shennan, Darren J. Dixon

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, …

Enantioselective Total Synthesis of (+)‐Incargranine A Enabled by Bifunctional Iminophosphorane and Iridium Catalysis

Anna Miller, Phillip Biallas, Benjamin D. A. Shennan, Darren J. Dixon

Abstract Herein we report the first enantioselective total synthesis of (+)‐incargranine A, in nine steps. The total synthesis was enabled by an enantioselective intramolecular organocatalysed desymmetrising Michael addition of a malonamate ester to a linked dienone substrate that established pivotal stereocentres with …

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Enantioselective Total Synthesis of (+)‐Incargranine A Enabled by Bifunctional Iminophosphorane and Iridium Catalysis

Anna Miller, Phillip Biallas, Benjamin D. A. Shennan, Darren J. Dixon

Herein we report the first enantioselective total synthesis of (+)-incargranine A, in nine steps. The total synthesis was enabled by an enantioselective intramolecular organocatalysed desymmetrising Michael addition of a malonamate ester to a linked dienone substrate that established pivotal stereocentres with excellent …

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1,2-Redox Transpositions of Tertiary Amides

Benjamin D. A. Shennan, Sergio Sánchez-Alonso, Gabriele Rossini, Darren J. Dixon

Reactions capable of transposing the oxidation levels of adjacent carbon atoms enable rapid and fundamental alteration of a molecule's reactivity. Herein, we report the 1,2-transposition of the carbon atom oxidation level in cyclic and acyclic tertiary amides, resulting in the one-pot synthesis …

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1,2-Redox Transpositions of Tertiary Amides

Benjamin D. A. Shennan, Sergio Sánchez Alonso, Darren J. Dixon

Reactions capable of transposing the oxidation levels of adjacent carbon atoms in organic molecules enable rapid and fundamental alteration of a molecule’s reactivity. Herein, we report the 1,2-transposition of carbon atom oxidation level in cyclic and acyclic tertiary amides, resulting in the …

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Bifunctional Iminophosphorane‐Catalyzed Enantioselective Nitroalkane Addition to Unactivated α,β‐Unsaturated Esters**

Daniel Rozsar, Alistair J. M. Farley, Iain McLauchlan, Benjamin D. A. Shennan et autres

Herein we describe the enantioselective intermolecular conjugate addition of nitroalkanes to unactivated α,β-unsaturated esters, catalyzed by a bifunctional iminophosphorane (BIMP) superbase. The transformation provides the most direct access to pharmaceutically relevant enantioenriched γ-nitroesters, utilizing feedstock chemicals, with unprecedented selectivity. The methodology exhibits …

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Bifunctional Iminophosphorane‐Catalyzed Enantioselective Nitroalkane Addition to Unactivated α,β‐Unsaturated Esters**

Daniel Rozsar, Alistair J. M. Farley, Iain McLauchlan, Benjamin D. A. Shennan et autres

Abstract Herein we describe the enantioselective intermolecular conjugate addition of nitroalkanes to unactivated α,β‐unsaturated esters, catalyzed by a bifunctional iminophosphorane (BIMP) superbase. The transformation provides the most direct access to pharmaceutically relevant enantioenriched γ‐nitroesters, utilizing feedstock chemicals, with unprecedented selectivity. The methodology …

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A New Organocatalytic Desymmetrization Reaction Enables the Enantioselective Total Synthesis of Madangamine E

Shinya Shiomi, Benjamin D. A. Shennan, Ken Yamazaki, Ángel L. Fuentes de Arriba et autres

High Resolution Image Download MS PowerPoint Slide The enantioselective total synthesis of madangamine E has been completed in 30 steps, enabled by a new catalytic and highly enantioselective desymmetrizing intramolecular Michael addition reaction of a prochiral ketone to a tethered β,β′ -disubstituted …

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