Design and syntheses of putative bioactive taxanes Original Research Article

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.