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Literature DB >> 21079876

A concise synthesis of the molecular framework of pleuromutilin.

Junjia Liu¹, Stephen D Lotesta, Erik J Sorensen.

Abstract

Two syntheses of the tricyclic carbon skeleton of pleuromutilin are reported. Diastereoselective 1,4-conjugate additions were used to elaborate bicyclic precursors at an early stage of each route, while ring-forming olefin metatheses were executed to complete the pleuromutilin carbon framework. The congeners prepared are appropriately functionalized to enable access to diverse pleuromutilin analogues.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2010 PMID： 21079876 PMCID： PMC3156455 DOI： 10.1039/c0cc04077k

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

14 in total

1. The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.

Authors: T M Trnka; R H Grubbs
Journal: Acc Chem Res Date: 2001-01 Impact factor: 22.384

2. Biochemical characterization of the interactions of the novel pleuromutilin derivative retapamulin with bacterial ribosomes.

Authors: Kang Yan; Lenore Madden; Anthony E Choudhry; Christine S Voigt; Robert A Copeland; Richard R Gontarek
Journal: Antimicrob Agents Chemother Date: 2006-08-28 Impact factor: 5.191

3. Metathesis reactions in total synthesis.

Authors: K C Nicolaou; Paul G Bulger; David Sarlah
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

Review 4. Mutilins derivatives: from veterinary to human-used antibiotics.

Authors: Changhua Hu; Yi Zou
Journal: Mini Rev Med Chem Date: 2009-10 Impact factor: 3.862

5. A dialdehyde cyclization cascade: an approach to pleuromutilin.

Authors: Matthew D Helm; Madeleine Da Silva; David Sucunza; Thomas J K Findley; David J Procter
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

6. Pleuromutilins. Fermentation, structure and biosynthesis.

Authors: F Knauseder; E Brandl
Journal: J Antibiot (Tokyo) Date: 1976-02 Impact factor: 2.649

7. New route to azaspirocycles via the organolithium-mediated conversion of beta-alkoxy aziridines into cyclopentenyl amines.

Authors: Stephen P Moore; Susannah C Coote; Peter O'Brien; John Gilday
Journal: Org Lett Date: 2006-10-26 Impact factor: 6.005

8. Some studies in the biosynthesis of terpenes and related compounds.

Authors: D Arigoni
Journal: Pure Appl Chem Date: 1968 Impact factor: 2.453

Review 9. Antibiotics for emerging pathogens.

Authors: Michael A Fischbach; Christopher T Walsh
Journal: Science Date: 2009-08-28 Impact factor: 47.728

10. New pleuromutilin derivatives with enhanced antimicrobial activity.II.Structure-activity correlations.

Authors: H Egger; H Reinshagen
Journal: J Antibiot (Tokyo) Date: 1976-09 Impact factor: 2.649

11 in total

1. Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of Medium to Large, P-Stereogenic Bicyclo[n.3.1]phosphates.

Authors: Soma Maitra; Jana L Markley; Rambabu Chegondi; Paul R Hanson
Journal: Tetrahedron Date: 2015-09-02 Impact factor: 2.457

2. Diastereoselective syntheses of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions.

Authors: Junjia Liu; Maurice A Marsini; T Aaron Bedell; Paul J Reider; Erik J Sorensen
Journal: Tetrahedron Date: 2016-03-15 Impact factor: 2.457

10. Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.

Authors: Rebecca E Ruscoe; Neal J Fazakerley; Huanming Huang; Sabine Flitsch; David J Procter
Journal: Chemistry Date: 2015-11-26 Impact factor: 5.236

A concise synthesis of the molecular framework of pleuromutilin.

1. The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.

2. Biochemical characterization of the interactions of the novel pleuromutilin derivative retapamulin with bacterial ribosomes.

3. Metathesis reactions in total synthesis.

Review 4. Mutilins derivatives: from veterinary to human-used antibiotics.

5. A dialdehyde cyclization cascade: an approach to pleuromutilin.

6. Pleuromutilins. Fermentation, structure and biosynthesis.

7. New route to azaspirocycles via the organolithium-mediated conversion of beta-alkoxy aziridines into cyclopentenyl amines.

8. Some studies in the biosynthesis of terpenes and related compounds.

Review 9. Antibiotics for emerging pathogens.

10. New pleuromutilin derivatives with enhanced antimicrobial activity.II.Structure-activity correlations.

1. Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of Medium to Large, P-Stereogenic Bicyclo[n.3.1]phosphates.

2. Diastereoselective syntheses of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions.

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

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

5. Phosphate-tether-mediated ring-closing metathesis for the preparation of complex 1,3-anti-diol-containing subunits.

Review 6. The evolving role of chemical synthesis in antibacterial drug discovery.

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

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

Review 9. Total synthesis of complex terpenoids employing radical cascade processes.

10. Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.