6533b823fe1ef96bd127e78e

RESEARCH PRODUCT

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

L. CamardaL. CerauloVita Di StefanoM. Ferrugia

subject

Settore CHIM/10 - Chimica Degli Alimentiatractyligenin-15β-OH epimerSettore CHIM/08 - Chimica Farmaceutica19-nor-kaurene compound

description

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.

http://hdl.handle.net/10447/445406