First synthesis of caerulomycin B. A new synthesis of caerulomycin C.
Caerulomycins produced by Streptomyces caeruleus are bipyridinic molecules endowed with antibiotic properties. The first synthesis of caerulomycin B (1) as well as a new synthesis of caerulomycin C (2) are reported. Starting from 3-hydroxypyridine, the same methodology was used to prepare both compounds 1 and 2. Efficiently controlled reactions such as metalation to allow the synthesis of 2,6-diiodo-3,4-dialkoxypyridines, which are key intermediates, and further halogen-lithium exchange and cross-coupling to reach the targets molecules 1 and 2 have been developed.
Mongin
Florence
F
Laboratoire de Chimie Organique Fine et Hétérocyclique, IRCOF, UMR 6014, Place E. Blondel, BP 08, 76131 Mont-Saint-Aignan Cédex, France.
Trécourt
François
F
Gervais
Bruno
B
Mongin
Olivier
O
Quéguiner
Guy
G
D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D006219:Halogens / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011725:Pyridines / Q000138:chemical synthesis; D011728:Pyridones / Q000138:chemical synthesis; D013302:Streptomyces / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D006219:Halogens; D011725:Pyridines; D011728:Pyridones; C466841:caerulomycin B; C466842:caerulomycin C; D015082:2,2'-Dipyridyl