Racemic hydroxylactones 11a and 11b were converted through the key aldehyde intermediate 21 into the C 6 -C 4 acid 22, showing all the necessary functionalities for the subsequent transformation into verapamil 1. Baker's yeast reduction of racemic ketolactone 8 provided enantiomerically pure 11a, close to the diastereoisomer 11b possessing 0.14 ee. The unusual chemical behaviour observed during the synthetic study, such as the conversion of 13 into 14 upon reaction with MeMgI and of 16 into 17 and 18 upon acid treatment, as well as the low yields of a few relevant steps might be due to the crowd of functionalities around the stereogenic carbon atom of the intermediates. This inhibited completion of the work in the optically active series.