A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions

Znabet, Anass; Polak, Marloes M; Janssen, Elwin; Kanter, Frans J. J. de; Turner, Nicholas J.; Orru, Romano V. A.; Ruijter, Eelco

doi:10.1039/c0cc02823a

Cited by 181 publications

(127 citation statements)

References 22 publications

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“…[122] Ruitjer and coworkers used two classic MCRsan Ugi reaction and a Passerini reaction -in the convergent synthesis of the antiviral drug telaprevir (Scheme 18). [123] The synthesis is also three times shorter than the original reported procedure. [124] Many chemists have developed carefully designed 'one-pot' consecutive sequences that unite multiple components.…”

Section: Multi-component Reactions (Mcrs)mentioning

confidence: 90%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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An increasing number of synthetic organic chemists are embracing the philosophy of efficiency. Herein we highlight multi-bond forming processes, which form two or more new covalent bonds in a single synthetic operation. Such processes, which have the ability to rapidly increase structural complexity, are preeminent in contemporary synthetic organic chemistry. In this short review we classify, analyse, and contrast contemporary multi-bond forming processes, frame these cutting edge contributions within a historical context, and speculate on likely future developments in the area.

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Section: Multi-component Reactions (Mcrs)mentioning

confidence: 90%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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“…The special properties of the enzyme facilitate the formation of carbon-carbon and carbon-heteroatom bonds under environmental conditions. The properties of the biocatalyst can be used in Multi Component Reactions (MCRs) [5][6][7][8][9][10][11]. Given the potential for the multicomponent syntheses in industry and medicinal chemistry, there is no better strategy than utilizing enzyme-catalyzed synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Immobilized Lipase on Fe3O4 Nanoparticles as Nano biocatalyst for the Synthesis of Benzothiazepine and Spirobenzothiazine Chroman Derivatives

Baharfar

Mohajer

2016

Catal Lett

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A retrievable nanostructure heterogeneous catalyst, based on lipase (lipase from the fungus Aspergillus niger), namely Fe 3 O 4 -bonded lipase (Fe 3 O 4 NPs@ lipase) was prepared in nano size and fully characterized by several techniques such as Fourier transform infrared spectroscopy, X-ray diffraction, Scanning electron microscopy, Transmission electron microscopy and Vibrating sample magnetometer. The retrievable nanostructure catalyst was asserted to be an efficient catalyst in the synthesis of benzothiazepine and spirobenzothiazine chroman derivatives through three-component reaction of coumarine-3-carboxylic acid derivatives, 2-aminothiophenol, and alkyl isocyanides at room temperature under mild conditions. Graphical Abstract

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“…Again, MAO-N-D5 was successful in oxidizing mesopyrrolidines to 1 -pyrrolines, which are valuable synthons for highly enantiopure (S)-proline analogs and (S)-α-amino nitriles (79). MAO-N-D5 and amine oxidation again were crucial in a shortened synthesis of the antihepatitis C drug telaprevir, in which a cyclic meso-amine, 3,4-cyclopentyl-pyrroline, was oxidized to leave the building block 3,4,-cis-substituted 1-pyrroline (80).…”

Section: Monoamine Oxidase N (Mao-n) For Deracemization Of Racemic Ammentioning

confidence: 99%

Biocatalysis: A Status Report

Bommarius

2015

Annu. Rev. Chem. Biomol. Eng.

139

101

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This review describes the status of the fields of biocatalysts and enzymes, as well as existing drawbacks, and recent advances in the areas deemed to represent drawbacks. Although biocatalysts are often highly active and extremely selective, there are still drawbacks associated with biocatalysis as a generally applicable technique: the lack of designability of biocatalysts; their limits of stability; and the insufficient number of well-characterized, ready-to-use biocatalysts. There has been significant progress on the following fronts: (a) novel protein engineering tools, both experimental and computational, have significantly enhanced the toolbox for biocatalyst development. (b) The deactivation of biocatalysts under various stresses can be described quantitatively via rational models. There are several cases of spectacular leaps of stabilization after accumulating all stabilizing mutations found in earlier rounds. The concept that stabilization against one type of stress commonly also stabilizes against other types of stress is now experimentally considerably better founded than a few years ago.

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A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions

Cited by 181 publications

References 22 publications

Multi-Bond Forming Processes in Efficient Synthesis

Multi-Bond Forming Processes in Efficient Synthesis

Synthesis and Characterization of Immobilized Lipase on Fe3O4 Nanoparticles as Nano biocatalyst for the Synthesis of Benzothiazepine and Spirobenzothiazine Chroman Derivatives

Biocatalysis: A Status Report

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