Subscribe to RSS
Synthesis of Pluraflavin A ”Aglycone"
B. J. D. Wright, J. Hartung, F. Peng, R. Van de Water, H. Liu, Q.-H. Tan, T.-C. Chou, S. J. Danishefsky*
Columbia University and Sloan-Kettering Institute for Cancer Research, New York, USA
25 May 2009 (online)
Pluraflavin A shows excellent potency against a large number of human tumor cell lines. It contains a C-glycosidic linkage at C10 and the hydroxyl methyl group at C5 is O-linked to a 3′-epi-vancosamine. The synthesis of puraflavin A ”aglycone" (IC50 = 18 nM) is noteworthy for the [3+2] cycloaddition of nitrile oxide A and olefin B to give isoxazoline C and its subsequent transformation into γ-pyrone E.