Scott Burley

WORK HISTORY

EDUCATION

SKILLS

ABOUT SCOTT BURLEY

Master\'s Degree in Synthetic Organic Chemistry with graduate level course work and research experience in Organic synthesis. Research projects consisting of development of a short library-optimized route to the ergoline skeleton. The route was designed and structured to introduce diversity late in the synthetic scheme allow for the ease of the creation of a new synthetic library. A highly functionalized pyridine ring was utilized for the creation of an (indolylmethyl)pyridine structure by a Fischer indole synthesis. Diverse substituents on the phenylhydrazine component thus become incorporated into the indole ring and are carried through the remaining synthetic steps. Immediately following the Fischer reaction, the ergoline skeleton is constructed via a palladium assisted intramolecular cyclization, and in the final steps of the scheme the pyridine ring is modified and reduced. The resulting library of ergolines promises to be an outstanding tool for investigating the pharmacology of neuroreceptors. Burley, S. D; Lam, V. V; Lakner, F. J; Bergdahl, B. M; Parker, M. A, New Route to the Ergoline Skeleton via Cyclization of 4-Unsubstituted Indoles. Org. Lett. 2013, 15, 2598.Secondly, A library-optimized route to a class of dihydropyranobenzimidazole inhibitors was designed previously. These inhibitors had earlier been shown to bind to the internal ribosome entry site (IRES) of the viral RNA, preventing initiation of translation. New inhibitors were proposed based on the reported X-ray crystal structure of the parent compound bound to the IRES. Utilizing the classic Gabriel synthesis and reductive amination, new alkylamino side chains were produced and introduced late into the synthetic route via a nucleophilic aromatic substitution reaction. The target molecules will then be made available to collaborators for bioassay and continuing refinement of side chain substituents. This refinement is expected to lead to improved binding affinity and selectivity.