Synthesis of a β-strand mimetic based on a pyridine scaffold
2006 (English)In: Tetrahedron, ISSN 0040-4020, Vol. 62, no 47, 10937-10944 p.Article in journal (Refereed) Published
A synthetic route to a 2,4-disubstituted pyridine as a potential β-strand mimetic has been developed and applied in the synthesis of a tripeptidomimetic of Leu-Gly-Gly. The pyridine scaffold replaces the central glycine, and is substituted with analogues of leucine and glycine in positions 4 and 2, respectively. 2-Fluoro-4-iodopyridine was chosen as the functionalized scaffold and was substituted with protected leucinal in position 4 via a Grignard exchange reaction using iso-propyl magnesium chloride. The glycine moiety was introduced in position 2 via a nucleophilic aromatic substitution reaction (SNAr) facilitated by microwave irradiation. The synthetic sequence involved 12 steps with an overall yield of 7%.
Place, publisher, year, edition, pages
2006. Vol. 62, no 47, 10937-10944 p.
β-Strand mimetic, 2-Aminopyridine, Grignard exchange reaction, Nucleophilic aromatic substitution
IdentifiersURN: urn:nbn:se:umu:diva-2275DOI: 10.1016/j.tet.2006.08.080OAI: oai:DiVA.org:umu-2275DiVA: diva2:140204