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Atractyligenin chemistry. Part 4: Synthesis of the 15β-ol epimer of atractyligenin

1996

The oxidation with PCC of atractyligenin 3, the aglicone of the toxic glycoside 1 isolated from Atractylis gummifera L., led to the 15-oxo-derivative 6, together with a small amount of 2,15-dioxoderivative 5, with a selective oxidation of the allylic 15-OH group of the molecule. Further reduction with NaBH4 and KOH hydrolysis gave stereoselectively the 15β-ol epimer of atractiligenin 9.