Azabicyclic ring systems not only constitute a critical skeletal motif found in a diverse range of alkaloid families but serve as structural scaffolds in synthetic molecules which display important pharmacological activities. As part of our ongoing study of the intramolecular oxamidation of unsaturated O-alkyl hydroxamates, we have investigated this process in the context of 1,3-enynes and 1,3,5-diynes. Iodine(III)-mediated cyclofunctionalization of these alkene substrates proceeds efficiently with high regio- and stereoselectivity to provide usefully functionalized azabicycles. Application of this versatile methodology to the preparation of the structural core of the class II Galbulimima alkaloid and potent muscarinic antagonist (-)-himandrine, will be presented.

Intramolecular oxamidation of 1,3-enynes and 1,3,5-diynes: A stereocontrolled route to usefully functionalized azabicyclic ring systems and beyond

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