Total synthesis of a biotinylated derivative of phorboxazole A via sonogashira coupling

TM Hansen, MM Engler, CJ Forsyth

Index: Hansen, T. Matthew; Engler, Mary M.; Forsyth, Craig J. Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 13 p. 2127 - 2130

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Citation Number: 36

Abstract

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 PdCl2 (PPh3) 2, CuI, and Et3N in THF. This process demonstrates the utility of mild carbon-carbon bond formation in the context of phorboxazoles' architecture ...