Nine modified compounds were synthesized by epoxidation, epoxide ring opening, lactonization and esterification reactions using dehydroepiandrosterone(DHEA) as starting material. The products were identified by NMR, MS and IR analysis. Furtherly, the preliminary antimicrobial activities of these compounds were evaluated. Two compounds exhibited moderate inhibition against Staphylococcus aureus. Six compounds showed moderate inhibition against Bacillus subtilis. Four compounds exhibited weak inhibition against Candida albicans.Keywords: dehydroepiandrosterone;chemical modification; synthesis;antimicrobial