'Decahydroquinoline construction through aza-annulation: A stereoselective synthesis of (±)-5-epipumiliotoxin C.'

Article abstract of DOI:10.1016/S0040-4039(00)61672-6

Aza-annulation of activated acrylic acid derivatives with 3-benzylamino-2-cyclohexenone led to the efficient formation of the corresponding bicyclic lactam. Stereospecific hydrogenation of this unsaturated lactam resulted in the selective formation of the cis fused bicyclic alkaloid, and subsequent elaboration at C-5 and C-2 completed the synthesis of the decahydroquinoline alkaloid (±)-5-epipumiliotoxin C.