Total synthesis of pentosidine.
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.
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA.
Adam J
AJ
Rosenberg
Daniel A
DA
Clark
D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011687:Purines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*
D011687:Purines; D011725:Pyridines; C064191:1H-imidazo(4,5-b)pyridine; D010165:Palladium; D001120:Arginine; C062187:pentosidine; D008239:Lysine