Literature DB >> 12556183

A concise synthesis of the tricyclic skeleton of pleuromutilin and a new approach to cycloheptenes.

Eric Bacqué1, François Pautrat, Samir Z Zard.   

Abstract

[reaction: see text] A short synthesis of the tricyclic skeleton of pleuromutilin is reported, featuring an unusually efficient 8-endo-trig radical cyclization of a xanthate precursor. In the course of this study, a one-carbon ring expansion leading to cycloheptenes was uncovered.

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Year:  2003        PMID： 12556183     DOI： 10.1021/ol027312m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  A concise synthesis of the molecular framework of pleuromutilin.

Authors:  Junjia Liu; Stephen D Lotesta; Erik J Sorensen
Journal:  Chem Commun (Camb)       Date:  2010-11-16       Impact factor: 6.222

2.  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

3.  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

4.  Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis.

Authors:  Stephen D Lotesta; Junjia Liu; Emma V Yates; Inna Krieger; James C Sacchettini; Joel S Freundlich; Erik J Sorensen
Journal:  Chem Sci       Date:  2011-04-14       Impact factor: 9.825

5.  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 6.  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

7.  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

8.  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 9.  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
  9 in total

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