SYNTHESIS OF (-) ��� PYRENOPHOROL ANTICANCER EVALUATION OF HETEROCYCLES

The total synthesis of (–)-pyrenophorol with high enantio selectivity has been accomplished in which the stereocenters were established by Jacobsen’s hydrolytic kinetic resolution and Sharpless asymmetric dihydroxylation and cyclization was achieved by intermolecular Mitsunobu cyclization. The compound 90b with electron donating 345-trimethoxy group on the phenyl ring showed excellent anticancer activity (MCF-7 = 0.018±0.0039 μM A549 = 0.011±0.0019 μM Colo-205 = 0.12±0.029 μM and A2780 = 0.17±0.023 μM) than etoposide. The compound 117i having electron-rich on the phenyl moiety showed greater anticancer property on all cell lines (PC3=0.11±0.068 μM; A549=0.18±0.063 μM; MCF-7= 0.52±0.074 μM and DU-145=0.17±0.082 μM).