Efforts Towards the Synthesis of Brianthein W

Abstract

The sphere of natural products is an abundant source of biologically active compounds. Because of this, there is a large body of research devoted to the study of interesting natural products as potential drugs or drug scaffolds. One natural product that may be biologically active is brianthein W, a diterpene that was originally isolated from the soft coral Briareum polyanthes. Other brianthein analogues have been shown to have medicinal qualities. For example, the 3- acetoxy analogue of brianthein W, brianthein A, has been shown to act on human carcinoma cell lines to reverse multidrug resistance. This multidrug resistance makes cancer treatment much more difficult, so the discovered effect of brianthein A is very desirable. The synthesis of brianthein W is of interest because it could contribute to efforts to study other possible medicinal effects of the brianthein analogues. Although brianthein W has been isolated in small amounts, the scale at which it has been obtained is not conducive to further study of this diterpene’s biological effects. However, since brianthein W’s structure has been determined, its total synthesis is one potential way to obtain this natural product in large enough amounts to facilitate the study of its possible medicinal qualities. As the total synthesis of brianthein W has not been previously explored, the purpose of this project is to work out a synthetic route to obtain this natural product. Beginning with readily available reagents and working through a proposed synthetic scheme, we have made progress toward the total organic synthesis of brianthein W.Bachelor of Scienc

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