Design and syntheses of putative bioactive taxanes

Article abstract of DOI:10.1016/S0968-0896(02)00066-4

Reduction of 5α-hydroxy-7β,9α,10β-triacetoxy-4(20), 11(12)-taxadien-13-one 1 with activated zinc in glacial acetic acid led to rearranged products, including compounds with double bonds at C3-C4, C10-C11 or with an epoxide at C11-C12. Molecular modeling studies suggested that addition of a side chain at C-20 or C-5 of the taxanes with a C3-C4 double bond might lead to bioactivity. Semi-syntheses and results of bioactivities are discussed.