Abstract
The stereospecific total synthesis of polyoxin C and the nucleoside analogue, uracil polyoxin C, is described. Condensation of (phenylthio) nitromethane with methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside gave a (Z)-nitro olefin. Addition of potassium trimethylsilanoate and ozonolysis gave an α-hydroxy thioester which was converted into polyoxin C and uracil polyoxin C via a azide and base incorporation using the Vorbruggen method
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