A strategic total synthesis that aims to access members of the Veratrum family of cevanine-type alkaloids. The Veratrum family of alkaloids all share a unique C-nor-D-homo [6-6-5-6] steroid skeleton and can be divided into three subtypes based on the connectivity to its piperdine ring with the cevanine-type being the largest subtype. The synthetic approach explored utilizes an asymmetric synthesis of a propargyl-substituted piperidinone fragment and an enantioselective synthesis of a bicyclic diyne fragment. After the unification of these two fragments an intramolecular [2+2+2] cycloisomerization reaction is performed creating three additional rings to offer total access to the Veratrum steroidal alkaloid family.