Monatshefte für Chemie - Chemical Monthly

, Volume 147, Issue 3, pp 509–521

Improved and scalable synthesis of building blocks for the modular synthesis of teraryl-based alpha-helix mimetics

Original Paper

DOI: 10.1007/s00706-015-1599-0

Cite this article as:
Trobe, M. & Breinbauer, R. Monatsh Chem (2016) 147: 509. doi:10.1007/s00706-015-1599-0
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Abstract

The modular synthesis of teraryl-based alpha-helix mimetics can be accomplished by sequential Suzuki-couplings of arylboronic acid building blocks with 4-iodophenyltriflate core-fragments. We report about new synthetic accesses to core fragments featuring the side chains of Leu, Lys, Cys, Glu, Gln, Ser, and Thr starting from simple phenol precursors.

Graphical abstract

Keywords

Baeyer–Villiger oxidation Claisen rearrangement Iodination Peptidomimetics Protein–protein interactions Wittig reaction 

Supplementary material

706_2015_1599_MOESM1_ESM.pdf (2.8 mb)
Supplementary material 1 (PDF 2877 kb)

Copyright information

© Springer-Verlag Wien 2015

Authors and Affiliations

  1. 1.Institute of Organic ChemistryGraz University of TechnologyGrazAustria

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