We have developed an alternative route to the azatricyclic core skeleton of FR901483 based on vinylation at the bridgehead position of 2-azabicyclo[3.3.1]nonane via an anti-Bredt iminiumion using vinylaluminum reagents.
Nucleophilic Alkylation on Anti-Bredt Iminium Ions. Facile Entry to the Synthesis of 1-Alkylated 2-Azabicyclo[3.3.1]nonanes (Morphans) and 5-Azatricyclo[6.3.1.0<sup>1,5</sup>]dodecane