Synthesis of (−)‐Mucocin Using a Diastereoselective Oxypalladation and Cross‐Metathesis

Synthesis of (−)‐mucocin isolated from Rollinia mucosa (Annonaceae) was achieved. Stereoselective construction of the tetrahydropyran (THP) ring moiety was performed using diastereoselective oxypalladation. The tetrahydrofuran (THF) ring moiety was prepared from ( S )‐(−)‐malic acid. The cross‐metathesis reaction between the THP and THF moieties afforded the nonadjacent THP–THF core part. Sonogashira cross‐coupling of the γ ‐lactone portion with the THP–THF core part followed by reduction of the enyne and removal of the protecting groups afforded (−)‐mucocin.