A series of potentially cytotoxic α,β-unsaturated γ -hydroxy-butyrolactones, -lactams and -thiolactones has been synthesized via regioselective hydride reduction of the appropriate maleic acid anhydrides, imides and thioanhydrides. By this means a straightforward access to naturally occurring antibiotic narthigenine 2, its hitherto unknown thio-analogue 5b and higher substituted derivatives and analogues of 2 is presented.