Synthesis
of (+)-muconin isolated from Rollinia mucosa (Annonaceae)
was achieved. Stereoselective construction of a tetrahydrofuran-terahydropyran
(THF-THP) ring moiety was performed using diastereoselective oxypalladation
in the presence of CuCl2. The cross-coupling reaction of
the THF-THP moiety with the γ-lactone portion followed by reduction
of the enyne and removal of the protecting groups afforded (+)-muconin.