Literature DB >> 20695449

Functionalization of aromatic amino acids via direct C-H activation: generation of versatile building blocks for accessing novel peptide space.

Falco-Magnus Meyer1, Spiros Liras, Angel Guzman-Perez, Christian Perreault, Jianwei Bian, Keith James.   

Abstract

Functionalized alpha-amino acid building blocks have been prepared in good yield with high regiocontrol and preservation of stereochemistry via iridium-catalyzed borylation of suitably protected aromatic alpha-amino acid derivatives. The utility of these systems in peptide couplings and Suzuki reactions has been demonstrated.

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Year:  2010        PMID： 20695449     DOI： 10.1021/ol1015674

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


  10 in total

1.  Synthesis of 2-D-L-Tryptophan by Sequential Ir-Catalyzed Reactions.

Authors:  Ravikrishna Vallakati; Abel T Plotnikov; Ryan A Altman
Journal:  Tetrahedron       Date:  2019-02-26       Impact factor: 2.457

2.  Generation of Broad-Spectrum Antifungal Drug Candidates from the Natural Product Compound Aureobasidin A.

Authors:  Peter G M Wuts; Lloyd J Simons; Brian P Metzger; Rachel C Sterling; Jerry L Slightom; Ake P Elhammer
Journal:  ACS Med Chem Lett       Date:  2015-04-23       Impact factor: 4.345

3.  Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.

Authors:  In-Soo Myeong; Nadide Hazal Avci; Mohammad Movassaghi
Journal:  Org Lett       Date:  2021-11-12       Impact factor: 6.072

4.  Bismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles.

Authors:  Fangyi Shen; Sriram Tyagarajan; Damith Perera; Shane W Krska; Peter E Maligres; Milton R Smith; Robert E Maleczka
Journal:  Org Lett       Date:  2016-03-21       Impact factor: 6.005

5.  Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.

Authors:  Alyssa H Antropow; Nicholas R Garcia; Kolby L White; Mohammad Movassaghi
Journal:  Org Lett       Date:  2018-06-04       Impact factor: 6.005

6.  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

7.  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

8.  The 2-(triphenylsilyl)ethoxycarbonyl-("Tpseoc"-) group: a new silicon-based, fluoride cleavable oxycarbonyl protecting group highly orthogonal to the Boc-, Fmoc- and Cbz-groups.

Authors:  Martin Golkowski; Thomas Ziegler
Journal:  Molecules       Date:  2011-06-07       Impact factor: 4.411

Review 9.  Indolylboronic Acids: Preparation and Applications.

Authors:  Marek Čubiňák; Tereza Edlová; Peter Polák; Tomáš Tobrman
Journal:  Molecules       Date:  2019-09-28       Impact factor: 4.411

10.  A Perspective on Late-Stage Aromatic C-H Bond Functionalization.

Authors:  Li Zhang; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2022-01-27       Impact factor: 15.419
  10 in total

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