Literature DB >> 29323492

Total Synthesis of (+)-Pleuromutilin.

Elliot P Farney1, Sean S Feng1, Felix Schäfers1, Sarah E Reisman1.   

Abstract

An 18-step synthesis of the antibiotic (+)-pleuromutilin is disclosed. The key steps of the synthesis include a highly stereoselective SmI2-mediated cyclization to establish the eight-membered ring and a stereospecific transannular [1,5]-hydrogen atom transfer to set the C10 stereocenter. This strategy was also used to prepare (+)-12-epi-pleuromutilin. The chemistry described here will enable efforts to prepare new mutilin antibiotics.

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Year:  2018        PMID： 29323492      PMCID： PMC5988231          DOI： 10.1021/jacs.7b13260

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  20 in total

1.  The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome.

Authors:  S M Poulsen; M Karlsson; L B Johansson; B Vester
Journal:  Mol Microbiol       Date:  2001-09       Impact factor: 3.501

2.  O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols.

Authors:  Jenna L Jeffrey; Jack A Terrett; David W C MacMillan
Journal:  Science       Date:  2015-08-27       Impact factor: 47.728

3.  Cyclopentanone ring-cleaved pleuromutilin derivatives.

Authors:  Dane M Springer; Amy Bunker; Bing-Yu Luh; Margaret E Sorenson; Jason T Goodrich; Joanne J Bronson; Kenneth DenBleyker; Thomas J Dougherty; Joan Fung-Tomc
Journal:  Eur J Med Chem       Date:  2006-12-06       Impact factor: 6.514

4.  Copper(I)/ABNO-catalyzed aerobic alcohol oxidation: alleviating steric and electronic constraints of Cu/TEMPO catalyst systems.

Authors:  Janelle E Steves; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2013-10-15       Impact factor: 15.419

5.  Total synthesis of (+)-pleuromutilin.

Authors:  Neal J Fazakerley; Matthew D Helm; David J Procter
Journal:  Chemistry       Date:  2013-04-15       Impact factor: 5.236

6.  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

7.  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

8.  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

9.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

10.  Simple, chemoselective hydrogenation with thermodynamic stereocontrol.

Authors:  Kotaro Iwasaki; Kanny K Wan; Alberto Oppedisano; Steven W M Crossley; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2014-01-15       Impact factor: 15.419
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  18 in total

1.  The High Chemofidelity of Metal-Catalyzed Hydrogen Atom Transfer.

Authors:  Samantha A Green; Steven W M Crossley; Jeishla L M Matos; Suhelen Vásquez-Céspedes; Sophia L Shevick; Ryan A Shenvi
Journal:  Acc Chem Res       Date:  2018-11-08       Impact factor: 22.384

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

3.  Re-engineering natural products to engage new biological targets.

Authors:  Stephen E Motika; Paul J Hergenrother
Journal:  Nat Prod Rep       Date:  2020-11-18       Impact factor: 13.423

4.  Fixing the Unfixable: The Art of Optimizing Natural Products for Human Medicine.

Authors:  Audrey E Yñigez-Gutierrez; Brian O Bachmann
Journal:  J Med Chem       Date:  2019-04-26       Impact factor: 7.446

5.  Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes.

Authors:  C Rose Kennedy; Hongyu Zhong; Rachel L Macaulay; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2019-05-16       Impact factor: 15.419

6.  Directed evolution of the rRNA methylating enzyme Cfr reveals molecular basis of antibiotic resistance.

Authors:  Kaitlyn Tsai; Vanja Stojković; Lianet Noda-Garcia; Iris D Young; Alexander G Myasnikov; Jordan Kleinman; Ali Palla; Stephen N Floor; Adam Frost; James S Fraser; Dan S Tawfik; Danica Galonić Fujimori
Journal:  Elife       Date:  2022-01-11       Impact factor: 8.140

7.  Total Synthesis of (-)-Maximiscin.

Authors:  Kyle S McClymont; Feng-Yuan Wang; Amin Minakar; Phil S Baran
Journal:  J Am Chem Soc       Date:  2020-05-01       Impact factor: 15.419

Review 8.  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.  Recent advances in the chemistry of ketyl radicals.

Authors:  Áron Péter; Soumitra Agasti; Oliver Knowles; Emma Pye; David J Procter
Journal:  Chem Soc Rev       Date:  2021-03-23       Impact factor: 54.564

10.  Synthetic studies toward longeracemine: a SmI2-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework.

Authors:  Keita Komine; Kyle M Lambert; Quentin R Savage; Joshua B Cox; John L Wood
Journal:  Chem Sci       Date:  2020-07-30       Impact factor: 9.825
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