Literature DB >> 12967293

Synthesis of a TMC-95A ketomethylene analogue by cyclization via intramolecular Suzuki coupling.

Markus Kaiser1, Carlo Siciliano, Irmgard Assfalg-Machleidt, Michael Groll, Alexander G Milbradt, Luis Moroder.   

Abstract

[structure: see text] A TMC-95A analogue extended at the C-terminus with NlePsi[COCH(2)]Gly-Ala-Ala-NH(2) was synthesized via side-chain cyclization of the linear precursor by a Suzuki cross-coupling reaction in solution to analyze the effect of additional P' residues on the inhibitory potency against yeast proteasome.

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Year:  2003        PMID： 12967293     DOI： 10.1021/ol035178f

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


  6 in total

1.  A concise, total synthesis of the TMC-95A/B proteasome inhibitors.

Authors:  Brian K Albrecht; Robert M Williams
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-26       Impact factor: 11.205

2.  Two-Steps Hantzsch Based Macrocyclization Approach for the Synthesis of Thiazole Containing Cyclopeptides.

Authors:  Adel Nefzi; Sergey Arutyunyan; Jason E Fenwick
Journal:  J Org Chem       Date:  2010-11-19       Impact factor: 4.354

3.  Development of a general, sequential, ring-closing metathesis/intramolecular cross-coupling reaction for the synthesis of polyunsaturated macrolactones.

Authors:  Scott E Denmark; Joseck M Muhuhi
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

4.  Direct C7 Functionalization of Tryptophan. Synthesis of Methyl (S)-2-((tert-Butoxycarbonyl)amino)-3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate.

Authors:  Kazuma Amaike; Richard P Loach; Mohammad Movassaghi
Journal:  Organic Synth       Date:  2015

5.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

6.  Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors.

Authors:  Grace E Hubbell; Jetze J Tepe
Journal:  RSC Chem Biol       Date:  2020-09-16
  6 in total

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