Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step
Dagmar Scharnagel, Imma Escofet, Helena Armengol‐Relats, M. Elena de Orbe, J. Nepomuk Korber, Antonio M. Echavarren
Abstract
Abstract The gold(I)‐catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)‐1,4‐disubstituted 1,3‐butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user‐friendly procedure. Reaction of acetylene with 1,5‐dienes gives rise stereoselectively to tricyclo[5.1.0.0 2,4 ]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone.
Topics & Concepts
AcetyleneCyclopropanationChemistryCatalysisLigand (biochemistry)Calcium carbideMedicinal chemistryAcetoneNatural productOrganic chemistryCombinatorial chemistryBiochemistryReceptorCatalytic Alkyne ReactionsSynthetic Organic Chemistry MethodsCyclopropane Reaction Mechanisms