Tandem intermolecular radical addition-rearrangement for azacycle synthesis

ORGN 134

David M. Hodgson and Shuji Hachisu. Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, United Kingdom
Addition of alkyl radicals to 2-sulfonyl-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1] heptadiene 1 led to the formation of 2-azabicycles 2 via tandem intermolecular radical addition – homoallylic radical rearrangement. This new methodology has been applied to the concise total syntheses of α-isokainic acid 3 and a known biologically active kainoid analogue 4. Efforts are underway to carry out the total synthesis of α-kainic acid 5.

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