Literature DB >> 23589420

Total synthesis of (+)-pleuromutilin.

Neal J Fazakerley1, Matthew D Helm, David J Procter.   

Abstract

The first enantiospecific total synthesis of the antibacterial natural product (+)-pleuromutilin has been achieved. The approach includes the synthesis of a non-racemic cyclisation substrate from (+)-trans-dihydrocarvone, a highly selective SmI2-mediated cyclisation cascade, an electron transfer reduction of a hindered ester, and the first efficient conversion of (+)-mutilin to the target.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID: 23589420     DOI: 10.1002/chem.201300968

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  23 in total

1.  Scalable procedure for the fragmentation of hydroperoxides mediated by copper and iron tetrafluoroborate salts.

Authors:  David Huang; Alexander W Schuppe; Michael Z Liang; Timothy R Newhouse
Journal:  Org Biomol Chem       Date:  2016-06-07       Impact factor: 3.876

Review 2.  Natural Products in the "Marketplace": Interfacing Synthesis and Biology.

Authors:  Benjamin J Huffman; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2019-02-13       Impact factor: 15.419

Review 3.  A brief history of antibiotics and select advances in their synthesis.

Authors:  Kyriacos C Nicolaou; Stephan Rigol
Journal:  J Antibiot (Tokyo)       Date:  2017-07-05       Impact factor: 2.649

4.  Total Synthesis of (+)-Pleuromutilin.

Authors:  Elliot P Farney; Sean S Feng; Felix Schäfers; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2018-01-17       Impact factor: 15.419

5.  Development of a Modular Synthetic Route to (+)-Pleuromutilin, (+)-12-epi-Mutilins, and Related Structures.

Authors:  Mingshuo Zeng; Stephen K Murphy; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2017-11-02       Impact factor: 15.419

6.  A modular and enantioselective synthesis of the pleuromutilin antibiotics.

Authors:  Stephen K Murphy; Mingshuo Zeng; Seth B Herzon
Journal:  Science       Date:  2017-06-02       Impact factor: 47.728

Review 7.  The evolving role of chemical synthesis in antibacterial drug discovery.

Authors:  Peter M Wright; Ian B Seiple; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-02       Impact factor: 15.336

8.  Scalable Synthesis of a Key Intermediate for the Production of Pleuromutilin-Based Antibiotics.

Authors:  Stephen K Murphy; Mingshuo Zeng; Seth B Herzon
Journal:  Org Lett       Date:  2017-08-31       Impact factor: 6.005

9.  Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

Authors:  Junjia Liu; T Aaron Bedell; Julian G West; Erik J Sorensen
Journal:  Tetrahedron       Date:  2016-01-28       Impact factor: 2.457

Review 10.  Total synthesis of complex terpenoids employing radical cascade processes.

Authors:  Kevin Hung; Xirui Hu; Thomas J Maimone
Journal:  Nat Prod Rep       Date:  2018-02-21       Impact factor: 13.423

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