A formal total synthesis of racemic sesquiterpenoid sativene.
Academic Article
Overview
abstract
Several key reactions involving intramolecular cyclization, Grignard reaction, and ionic hydrogenation have been employed in a formal synthesis of sativene. The synthesis affords 3-isopropyl-6-methyltricyclo[4.4.0.0(2,8)]decan-7-one, 12, McMurry's penultimate precursor to sativene, in 28% overall yield in eight steps starting with the commercially available racemic Wieland--Miescher ketone.