A short and efficient total synthesis of (+)-chinensiolide B is reported, starting from commercially available α-santonin. This strategy could be used for rapid preparation of chinensiolides and their derivative for further structure activity relationship studies.
Ad irect cyanation of benzyl ethers and 1,3-diarylpropenesw ith TMSCNw as performed under solvent-and metal-free conditions.T hiso xidative cross dehydrative coupling (CDC) reaction was promoted by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and providedr apid access to ab roadr ange of nitriles in good to excellent yields.
20 guaianolide derivatives 1~20 and 6-epi-santonin were synthesized from α-santonin through rearrangement, oxidation, and reduction, hydrolysis. The structures of all compounds were characterized by 1 H NMR, 13 C NMR and MS. The cell proliferation inhibiting activities of the target compounds were evaluated against A549 and HepG2 cell lines by thiazolyl blueterazolium bromide (MTT) method. The results showed that the epoxy guaiane 9 had obvious inhibitory effect on A549 and HepG2 cell lines with IC 50 values of (14.5±0.1), (10.6±0.3) μmol/L while epoxy guaiane 15 showed IC 50 values of (6.4±1.3) and (8.1±0.7) μmol/L.
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