The fragmentation of ?-silyloxy-�-hydroxy-a-diazocarbonyl compounds provides tethered aldehyde ynoates, which readily react with amino acids to provide polycyclic 2,5-dihydropyrroles via an intramolecular azomethine ylide 1,3-dipolar cycloaddition. Application of this reaction sequence in the synthesis of the steroidal alkaloid demissidine and the ergot alkaloid cycloclavine will be discussed.

Application of a ring fragmentation/azomethine ylide 1,3-dipolar cycloaddition sequence in alkaloid natural product synthesis

246th National Meeting (2013)

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