Natural products have become increasingly sought after as ecologically safer alternatives to herbicides and pesticides, as well as a source of new medicines. However, the biological activity of these compounds is often affected by their stereochemistry, lipophilicity and other factors. Slight modifications can alter the bioactivity either positively or negatively. Capsidiol is the principal phytoalexin of Capsicum annuum. As part of a structure -activity investigation of this phytoalexin, acetylcapsidiol was synthesized and tested in vitro for antifungal activity. Acetyl capsidiol was found to have a low inhibition effect on Aspergillus niger mycelial growth and spore germination. The results suggest that OH groups are indispensable for activity.