SYNTHESIS OF ARIZONIN C1

The first syntheses of the pyranonaphthoquinone antibiotics 5-epi-ariz onin B1 16, 5-epi-arizonin C1 15 and arizonin C1 3 are described. The key steps involve addition of 2-trimethylsilyloxyfuran 12 to the 2-ace tylnaphthoquinone 11 affording the adduct 13 which undergoes oxidative rearrangement to a pyranonaphthoquinone system 14 upon treatment with eerie ammonium nitrate. The regioselective synthesis of naphthoquinon e 11 cia oxidation of ketone 10 is described wherein 10 is prepared vi a addition of furan to 3,4-dimethoxydehydrobenzene followed by treatme nt with acid.