Synthetic approaches to racemic porantheridine and 8-epihalosaline via a nitroso Diels-Alder cycloaddition/ring-rearrangement metathesis sequence.

  title={Synthetic approaches to racemic porantheridine and 8-epihalosaline via a nitroso Diels-Alder cycloaddition/ring-rearrangement metathesis sequence.},
  author={Pierre Sancibrao and Delphine Karila and Cyrille Kouklovsky and Guillaume Vincent},
  journal={The Journal of organic chemistry},
  volume={75 12},
The application of a sequence involving a nitroso Diels-Alder cycloaddition and a ring-rearrangement metathesis to the total synthesis of (+/-)-8-epihalosaline and the formal synthesis of (+/-)-porantheridine is described. The formation of the 2,6-trans-disubstituted piperidine backbone of porantheridine has been accomplished by addition of a Grignard reagent onto an N-benzylpiperidone followed by a highly diastereoselective reduction of the imminium intermediate in one pot. 
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