Literature DB >> 20856952

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

Anass Znabet1, Marloes M Polak, Elwin Janssen, Frans J J de Kanter, Nicholas J Turner, Romano V A Orru, Eelco Ruijter.   

Abstract

A very short and efficient synthesis of the important drug candidate telaprevir, featuring a biocatalytic desymmetrization and two multicomponent reactions as the key steps, is presented. The classical issue of lack of stereoselectivity in Ugi- and Passerini-type reactions is circumvented. The atom economic and convergent nature of the synthetic strategy require only very limited use of protective groups.

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Year:  2010        PMID: 20856952     DOI: 10.1039/c0cc02823a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  17 in total

1.  Biocatalytic retrosynthesis.

Authors:  Nicholas J Turner; Elaine O'Reilly
Journal:  Nat Chem Biol       Date:  2013-05       Impact factor: 15.040

2.  Modern Multicomponent Reactions for better Drug Syntheses**

Authors:  Tryfon Zarganes-Tzitzikas; Alexander Dömling
Journal:  Org Chem Front       Date:  2014-09-01       Impact factor: 5.281

3.  Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure.

Authors:  Eman M M Abdelraheem; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling
Journal:  J Org Chem       Date:  2016-09-15       Impact factor: 4.354

4.  Synthesis of fused polycyclic β-carboline derivatives using Ugi-4CR followed by cascade cyclization.

Authors:  Vipin Kumar; Anjali Saxena; Ranjan Patra; Devalina Ray; Hong-Yu Li; Biswajit Saha
Journal:  Mol Divers       Date:  2022-06-02       Impact factor: 2.943

Review 5.  Chemical Conjugation in Drug Delivery Systems.

Authors:  Alexis Eras; Danna Castillo; Margarita Suárez; Nelson Santiago Vispo; Fernando Albericio; Hortensia Rodriguez
Journal:  Front Chem       Date:  2022-05-26       Impact factor: 5.545

6.  Automated and Accelerated Synthesis of Indole Derivatives on a Nano-Scale.

Authors:  Shabnam Shaabani; Ruixue Xu; Maryam Ahmadianmoghaddam; Li Gao; Martin Stahorsky; Joe Olechno; Richard Ellson; Michael Kossenjans; Victoria Helan; Alexander Dömling
Journal:  Green Chem       Date:  2018-12-21       Impact factor: 10.182

7.  Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts.

Authors:  Wolfgang Kroutil; Eva-Maria Fischereder; Christine S Fuchs; Horst Lechner; Francesco G Mutti; Desiree Pressnitz; Aashrita Rajagopalan; Johann H Sattler; Robert C Simon; Elina Siirola
Journal:  Org Process Res Dev       Date:  2013-04-22       Impact factor: 3.317

8.  Coupling Interrupted Fischer and Multicomponent Joullié-Ugi to Chase Chemical Diversity: from Batch to Sustainable Flow Synthesis of Peptidomimetics.

Authors:  Antonella Ilenia Alfano; Elisabetta Buommino; Maria Grazia Ferraro; Carlo Irace; Angela Zampella; Heiko Lange; Margherita Brindisi
Journal:  ChemMedChem       Date:  2021-10-18       Impact factor: 3.540

9.  Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi-Joullié reaction.

Authors:  Alessandro Pinna; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva; Valeria Rocca; Luca Banfi
Journal:  RSC Adv       Date:  2020-01-03       Impact factor: 3.361

Review 10.  Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics.

Authors:  Gijs Koopmanschap; Eelco Ruijter; Romano Va Orru
Journal:  Beilstein J Org Chem       Date:  2014-03-04       Impact factor: 2.883

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