A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis.
[reaction: see text] Enyne metathesis has been used to prepare bridged azabicycles and applied in a short asymmetric synthesis of the tropane ferruginine. A Grubbs first generation catalyst proved to be superior to the second generation catalyst in the enyne metathesis reaction.
Aggarwal
Varinder K
VK
School of Chemistry, Bristol University, Cantock's Close, Bristol BS8 1TS, U.K. v.aggarwal@bristol.ac.uk
Astle
Christopher J
CJ
Rogers-Evans
Mark
M
D000480:Alkynes / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D008968:Molecular Conformation; D010084:Oxidation-Reduction
D000480:Alkynes; D019086:Bridged Bicyclo Compounds, Heterocyclic; C418212:ferruginine