Approaches to taxol and taxol analogs through elaboration of aromatic C-ring precursors

A 21-step synthetic route to an enone known to be a taxoid precursor from pinene was developed as part of an effort to obtain access to the tricarbocyclic taxane core of taxol and its analogs via functionalization of its B and C rings. The procedure allows access to C1 oxidized intermediates, selective incorporation of substituents at C8 and oxidation at the C5 and C10 sites to afford 7-deoxy and 7,8-cyclopropyltaxol analogs.