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Short syntheses of the quinolizidine alkaloids lupinine and epilupinine via alkyl 3-(2-thioxo-1- piperdinyl)propanoates and the vinylogous urethanes prepared from them are reported. Alkyl piperidin-2-ylideneacetates were found to undergo reduction of the C=C bond with lithium aluminium hydride more readily than their pyrrolidin-2-ylideneacetate analogues, a finding that is in line with reports of the relative reactivities of double bonds exocyclic to five- and six- membered rings.

Influence of ring size on the reduction of vinylogous urethanes. Applications to the synthesis of lupinine and epilupinin