Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 28, Pages 6404-6419Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300877
Keywords
Synthetic methods; Cross-coupling; Nitrogen heterocycles; Peptides
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Funding
- Spanish Science and Innovation Ministry (CICYT) [CTQ2009-07758, CTQ2012-30930]
- Generalitat de Catalunya [2009SGR 1024]
- Instituto de Salud Carlos III (ISCIII)
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The scope of 2,6-dichloronicotinic acid as a precursor of thiopeptide polyheterocylic cores has been extensively studied in a cross-coupling-based approach. Differentiation of the two chlorinated positions under SNAr conditions and versatility of the carboxylic acid are key for the preparation of 2,3,6-trisubstituted pyridines with complete regiocontrol. With the present strategy, nine different azole-substituted pyridines were synthesized. Studies towards the selective deprotection of their functionalities resulted in a set of fully orthogonal protecting groups that permits the elongation of all three pyridine substituents.
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