Sulikowski Research

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Total Synthesis of Complex Natural Products

Chemical Biology of Natural Products

A longstanding interest of the Sulikowski research group is the total synthesis of structurally complex natural products.  The selection of natural products as synthetic targets is based on structural novelty, scarcity in nature and/or biological activity.  Among these three selection criteria structure novelty is of paramount importance, as this often leads to the development of novel synthetic design and strategy.  Natural products of current interest to the Sulikowski group are shown below and include heterocyclic (bielschowskysin and upenamide), polyketide (ammocidin D), aromatic polyketide (hibarimicinone and lomaiviticinone) and lipid derived (bicyclobutane fatty acid) synthetic targets.  To date, we have completed the synthesis of urdamycinone B, (+)-SF 2315A, (+)-5-epiindolizidine 167B, landomycin A hexasaccharide, apoptolidinone, (+)-haliclonacyclamine C and bicyclobutane fatty acid.

 

In addition to the total synthesis of natural products we are also investigating various aspects of chemical biology associated with this fascinating group of small molecules (natural products) discovered in living systems.  Our interests can be generally divided into two areas.  First, we aim to define biosynthetic pathways leading to complex natural products.  And consider if this method of assembly can be taken to our advantage in the laboratory preparation of natural products and derivatives.  For example, we have studied the biosynthesis of phomoidride B (which involves the remarkable dimerization-oxidation pathway starting from a simple unsaturated anhydride). In collaboration with the Bachmann group we are also studying the biosynthesis of the cell-selective cytotoxic macrolide apoptoldin A.  A second area of interest is the discovery and study of the effects of natural products on biological systems, including cell cytotoxicity and interaction with cellular targets.  A majority of these studies are conducted in collaboration with members of the Vanderbilt Institute of Chemical Biology.