The goal of this dissertation was to carry out synthesis of condensed heterocyclic analogues of a lead compound via domino Knoevenagel-hetero-Diels-Alder reaction, for evaluation of their antiproliferative activities. Starting from 4-methoxyphenol, starting material of the domino cyclization was prepared in four steps. Beta di-carbonyl reagents were reacted with these derivatives to produce ten condensed chiral O-heterocycles for pharmacological studies. The preliminary antiproliferative test of compound 87a on A2780 (ovarian carcinoma) and WM35 (melanoma) showed improvement relative to the original compound.