Isomerization, autooxidation and epimerization for the introduction of C-1 to C-5 functionality into the taxane ABC ring system

Article abstract of DOI:10.1016/S0040-4039(96)01495-5

Treatment of 2-ketotax-3-enes with t-BuOK/t-BuOH/THF/65°C results in isomerization of the double bond into the 4,5-position and a trans-B/C ring fusion. Subsequent exposure to t-BuOK/THF/P(OEt)₃ introduces the C-1-hydroxyl group.