Total synthesis of a biotinylated derivative of phorboxazole A via sonogashira coupling.
The C46 terminus of phorboxazole A has been modified to incorporate a biotin-terminated linker via direct palladium-mediated Sonogashira reaction conditions. Synthetic 45,46-dehydrobromophorboxazole A was joined with a tris-(polyethyleneglycol)vinyl iodide-biotin ester using catalytic PdCl(2)(PPh(3))(2), CuI, and Et(3)N in THF. This process demonstrates the utility of mild carbon-carbon bond formation in the context of phorboxazoles' architecture and provides a potential affinity probe.
Hansen
T Matthew
TM
Department of Chemistry, University of Minnesota, 207 Pleasant ST S.E., 55455, Minneapolis, MN, USA.
Engler
Mary M
MM
Forsyth
Craig J
CJ
D000935:Antifungal Agents / Q000138:chemical synthesis*; D001710:Biotin / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared
D000935:Antifungal Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D010080:Oxazoles; C408887:phorboxazole A; D001710:Biotin