Successful synthesis of unsymmetrical linear diarylheptanoids with syn-1,3-diol unit and their enantiomers have been achieved using acyl anion and Wittig olefination chemistry. The syn disposition of the two hydroxyl groups in the linear diarylheptanoids was achieved with the use of d-xylose as starting material. The synthesized compounds were tested for anti-proliferative activity on HeLa cells using MTT assay at 50 µm concentration. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim