Biomimetic Total Synthesis of (±)-Doitunggarcinone A and (+)-Garcibracteatone

A full
account of our oxidative radical cyclization approach to
the synthesis of garcibracteatone and doitunggarcinone A is presented.
This includes the first enantioselective synthesis of garcibracteatone,
which allowed the absolute configuration of the natural compound to
be determined. The first synthesis of doitunggarcinone A is also described,
which confirms our reassignment of the relative configuration of this
molecule. Novel syntheses of monoterpene fragments used to construct
the target molecules are also reported.