Since it has been reported that Dynemicin A, which consists of enediyne functions, has a DNA cleavage activity, it is increasing interested in the synthesis of enediyne compounds and the utilization of their compounds as an antitumor antibiotic agent. In the course of our study on the synthesis of artificial bioactive molecules, we tried to synthesize the enediyne compound 1 as the Dynemicin A analogue core molecule. Lactone moiety of 1 can be converted into a various functional groups. And above, affinity moieties for DNA (DNA intercalators, DNA minor groove binders etc.) or various saccharides (with the ability of cytorecognition) can be introduced into the molecules by the reaction of functional groups with various reagents. In this presentation, we show the synthesis of the core molecule 1 and various bifunctionalized core molecules 12-17 based on the various transformations of the lactone moiety of 1. After then, the epoxydation of the molecules 1, cis-1, 15, cis-15, 16, and 17 with mCPBA was carried out and we investigated the DNA clevage activity of these epoxides 18, cis-18, 19, cis-19, 20, and 21. On the basis of the informations obtained from the DNA cleavage activity of 18-21, we synthesized several hybrid models having various functional moiety (affinity moiety for DNA or saccharides) and investigated the DNA clevage activity of these hybrid models.