Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy

@inproceedings{Coldham2012SynthesisOF,
  title={Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy},
  author={Iain Coldham and Adam J M Burrell and H{\'e}l{\`e}ne D S Guerrand and Luke Watson and Nathaniel G. Martin and Niall Oram},
  booktitle={Beilstein journal of organic chemistry},
  year={2012}
}
Heating aldehydes that contain a protected hydroxymethyl group, a tethered alkyl chloride and a tethered alkenyl group at the α-position of the aldehyde with an amine sets up a cascade (tandem) reaction sequence involving condensation to an intermediate imine, then cyclization and formation of an intermediate azomethine ylide and then intramolecular dipolar cycloaddition. The fused tricyclic products are formed with complete or very high stereochemical control. The hydroxymethyl group was… CONTINUE READING