Two-Phase Synthesis of (−)-Taxuyunnanine D

The first successful effort to replicate
the beginning of the Taxol
oxidase phase in the laboratory is reported, culminating in the total
synthesis of taxuyunnanine D, itself a natural product. Through a
combination of computational modeling, reagent screening, and oxidation
sequence analysis, the first three of eight C–H oxidations
(at the allylic sites corresponding to C-5, C-10, and C-13) required
to reach Taxol from taxadiene were accomplished. This work lays a
foundation for an eventual total synthesis of Taxol capable of delivering
not only the natural product but also analogs inaccessible via bioengineering.