Literature DB >> 22208950

Direct, regioselective, and chemoselective preparation of novel boronated tryptophans by Friedel-Crafts alkylation.

Silvia Bartolucci1, Francesca Bartoccini, Marika Righi, Giovanni Piersanti.   

Abstract

A facile synthetic approach to the direct preparation of various novel unnatural boronated protected tryptophans using a regio- and chemoselective electrophilic substitution of 4- and 5-boronated indoles with N-protected dehydroalanine is described. The gram-scale synthesis of two free tryptophan boronic acids is also reported.
© 2011 American Chemical Society

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Year:  2011        PMID: 22208950     DOI: 10.1021/ol203216h

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


  7 in total

1.  De novo synthesis of alkyne substituted tryptophans as chemical probes for protein profiling studies.

Authors:  R N Nair; J J Rosnow; T A Murphree; M E Bowden; S R Lindemann; A T Wright
Journal:  Org Chem Front       Date:  2016-12-26       Impact factor: 5.281

Review 2.  Dehydroamino acids: chemical multi-tools for late-stage diversification.

Authors:  Jonathan W Bogart; Albert A Bowers
Journal:  Org Biomol Chem       Date:  2019-04-10       Impact factor: 3.876

3.  Photocatalytic Reductive Olefin Hydrodifluoroalkylation Enabled by Tertiary Amine Reductants Compatible with Complex Systems.

Authors:  Jonathan D Ellefsen; Scott J Miller
Journal:  J Org Chem       Date:  2022-07-13       Impact factor: 4.198

4.  Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.

Authors:  Chun-Ming Chio; Ying-Cheng Huang; You-Cheng Chou; Fu-Chun Hsu; Yen-Buo Lai; Chung-Shan Yu
Journal:  ACS Med Chem Lett       Date:  2020-03-16       Impact factor: 4.345

Review 5.  Indolylboronic Acids: Preparation and Applications.

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

6.  Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration.

Authors:  Michele Mari; Simone Lucarini; Francesca Bartoccini; Giovanni Piersanti; Gilberto Spadoni
Journal:  Beilstein J Org Chem       Date:  2014-08-26       Impact factor: 2.883

7.  Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents.

Authors:  Raffaella Campana; Alessio Merli; Michele Verboni; Francesca Biondo; Gianfranco Favi; Andrea Duranti; Simone Lucarini
Journal:  Pharmaceuticals (Basel)       Date:  2019-12-17
  7 in total

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