An Enantioselective Synthesis of the CE Ring System of the Alkaloids Manzamine A, E and F, and Ircinal A

Article abstract of DOI:10.1016/0040-4039(95)00296-O

An efficient enantioselective synthesis of the azabicyclo<6.3.0>undecane 6, corresponding to the CE ring system found in the manzamines A,E, and F, and ircinal A, from (S)-prolinol is described.The key step in the route to 6 was the intramolecular generation and rearrangement of the spiro-fused bicyclic ylide 5 from a copper carbenoid.