Literature DB >> 10804559

Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling.

M S Jensen1, C Yang, Y Hsiao, N Rivera, K M Wells, J Y Chung, N Yasuda, D L Hughes, P J Reider.   

Abstract

[formula: see text] A short synthesis of carbapenem 1 is described. They key step involves the cross-coupling of an enol triflate with an amino-substituted sp3 carbon. This cross-couping, which allows the introduction of the complete side chain in one step, utilizes a stannatrane as the heteroalkyl transfer reagent.

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Year:  2000        PMID： 10804559     DOI： 10.1021/ol005641d

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


  10 in total

1.  Stereospecific Palladium-Catalyzed Acylation of Enantioenriched Alkylcarbastannatranes: A General Alternative to Asymmetric Enolate Reactions.

Authors:  Chao-Yuan Wang; Glenn Ralph; Joseph Derosa; Mark R Biscoe
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-16       Impact factor: 15.336

2.  Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

Authors:  Xinghua Ma; Mohamed Diane; Glenn Ralph; Christine Chen; Mark R Biscoe
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-04       Impact factor: 15.336

3.  Synthesis and anticancer activity of all known (-)-agelastatin alkaloids.

Authors:  Sunkyu Han; Dustin S Siegel; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

4.  Pd-catalyzed cross-coupling of α-(acyloxy)-tri-n-butylstannanes with alkenyl, aryl, and heteroaryl electrophiles.

Authors:  Mohan Goli; Anyu He; J R Falck
Journal:  Org Lett       Date:  2010-12-09       Impact factor: 6.005

5.  Preparation of Enantioenriched Alkylcarbastannatranes via Nucleophilic Inversion of Alkyl Mesylates for Use in Stereospecific Cross-Coupling Reactions.

Authors:  Glenn Ralph; Mark R Biscoe
Journal:  Organometallics       Date:  2019-09-03       Impact factor: 3.876

6.  Reinvestigation of aminomethyltrifluoroborates and their application in Suzuki-Miyaura cross-coupling reactions.

Authors:  Jessica Raushel; Deidre L Sandrock; Kanth V Josyula; Deborah Pakyz; Gary A Molander
Journal:  J Org Chem       Date:  2011-03-15       Impact factor: 4.354

7.  Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.

Authors:  Gary A Molander; Belgin Canturk
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 8.  Potassium trifluoroborate salts as convenient, stable reagents for difficult alkyl transfers.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  Curr Opin Drug Discov Devel       Date:  2009-11

9.  Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  Org Lett       Date:  2007-03-17       Impact factor: 6.005

10.  Stereoretentive Pd-catalysed Stille cross-coupling reactions of secondary alkyl azastannatranes and aryl halides.

Authors:  Ling Li; Chao-Yuan Wang; Rongcai Huang; Mark R Biscoe
Journal:  Nat Chem       Date:  2013-05-19       Impact factor: 24.427
  10 in total

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