This thesis describes the synthesis of bioactive benzofuran compounds using the halogen-metal exchange reaction. The first portion shows a methodological study in which we investigated the limits of the reaction, comparing the yields we obtained to those already known in the literature. The second portion shows the implementation of the halogen-metal exchange reaction en route to two natural products. The first natural product, 2-[4,5-dimethoxy-2-(3-phenyl-trans-allyloxy)benzyl]-5-hydroxy-6-methoxy-3-phenylbenzofuran, has been characterized as an antiandrogenic compound showing moderate inhibitory activity against testosterone 5[Alpha]-reductase, an enzyme responsible for converting testosterone into 5[Alpha]-dihydrotestosterone (DHT). In addition to the cyclization, this work highlights an intriguing etherification reaction with deuterated chloroform. The second natural product, isoparvifuran, shows antifungal activity. This work represents the first reported synthesis of 2-[4,5-dimethoxy-2-(3-phenyl-trans-allyloxy)benzyl]-5-hydroxy-6-methoxy-3-phenylbenzofuran and the second reported synthesis of isoparvifuran.