Synthesis of a diterpene taxoid skeleton, bicyclo[9.3.1]pentadecatriene

Article abstract of DOI:10.1016/S0040-4020(98)00334-2

The synthesis of bicyclo[9.3.1]pentadecatriene skeleton was investigated by employing cyclization reactions using two key precursors bearing acetylene cobalt complex. Cyclization for the synthesis of strained twelve-membered ring was achieved via Nicholas type reaction in reasonable yield. Reductive decomplexation of the dicobalt hexacarbonyl moiety of the cyclization product was achieved with n-Bu₃SnH in the presence of a catalytic amount of NBS in 1,4-cyclohexadiene solvent.