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Synfacts 2009(6): 0593-0593  
DOI: 10.1055/s-0029-1216676
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Pluraflavin A ”Aglycone"

Contributor(s): Philip Kocienski, Indu Dager
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
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Publikationsdatum:
25. Mai 2009 (online)

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Significance

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.