Total synthesis of pentosidine

Adam J Rosenberg; Daniel A Clark

doi:10.1021/ol3021226

Total synthesis of pentosidine

Org Lett. 2012 Sep 7;14(17):4678-81. doi: 10.1021/ol3021226. Epub 2012 Aug 21.

Authors

Adam J Rosenberg¹, Daniel A Clark

Affiliation

¹ Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA.

PMID: 22909052
DOI: 10.1021/ol3021226

Abstract

Pentosidine, a biologically important advanced glycation endproduct, has been accessed in a rapid, high-yielding manner. The synthesis was accomplished via a six-step sequence starting with 3-amino-2-chloropyridine and features a palladium-catalyzed tandem cross-coupling/cyclization to construct the imidazo[4,5-b]pyridine core.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Arginine / analogs & derivatives*
Arginine / chemical synthesis
Arginine / chemistry
Catalysis
Cyclization
Lysine / analogs & derivatives*
Lysine / chemical synthesis
Lysine / chemistry
Molecular Structure
Palladium / chemistry
Purines / chemistry*
Pyridines / chemistry*

Substances

Purines
Pyridines
1H-imidazo(4,5-b)pyridine
Palladium
Arginine
pentosidine
Lysine