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From 2,6‐Dichloronicotinic Acid to Thiopeptide Cores
Author(s) -
JustBaringo Xavier,
Albericio Fernando,
Álvarez Mercedes
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300877
Subject(s) - chemistry , pyridine , carboxylic acid , scope (computer science) , stereochemistry , combinatorial chemistry , regioselectivity , organic chemistry , catalysis , computer science , programming language
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 S N Ar 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.