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 sixmembered rings.