Investigation of a Tandem 6-exo Cyclization/Claisen Rearrangement Sequence as a Route to Cyclooctane Containing Bioactive Natural Products

By: Victoria Iannarone '15

Advising Faculty: Timo Ovaska

Eight-membered carbocyclic compounds (cyclooctanoids) are widespread in Nature and many of them exhibit significant biological properties, including anti-tumor and antibacterial activity. They have been isolated from various natural sources, such as marine organisms, pathogenic fungi, terrestrial plants and insects. To date, well over 100 structurally diverse cyclooctanoid natural products with varying degrees of complexity have been identified and characterized. Despite their natural abundance and therapeutic potential, compounds that incorporate eight-membered ring structures are difficult to synthesize in the laboratory. However, laboratory synthesis of these compounds is essential for full evaluation of their biological activity. To this end, our group has recently developed a concise reaction sequence that allows the efficient conversion of appropriately substituted acetylenic allyl alcohols to several cyclooctane-containing ring systems. The aim of this research is to gain a deeper mechanistic understanding of these reactions and to use the chemistry that has been developed to synthesize several biologically relevant cyclooctanoid natural products.

Related Fields: Chemistry, Chemistry/ Biochemistry, Environmental Chemistry