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Wednesday, April 22 • 12:40pm - 1:00pm
Synthesis of the Ficellomycin Core using a Late-Stage [3+2]-azide Alkene Cycloaddition

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Antibiotics are crucial for fighting bacterial infections, and many antibiotics are produced by bacteria in an effort to destroy their competition. Researchers have developed methods for isolating and modifying antibiotic compounds so that they can be used to treat bacterial infections in humans. One such compound, ficellomycin, which was first isolated from the Streptomyces ficellus bacterium in the 1970’s, has been found to inhibit the growth of many Gram-positive bacteria, including some antibiotic-resistant organisms. Since its isolation, research on ficellomycin’s synthesis and mechanism of action has been limited because of its highly unstable azabicyclo[3.1.0]hexane core. The objective of this research was to synthesize the core of ficellomycin from L-serine and to investigate the use of a late-state [3+2]-azide alkene cycloaddition to construct the azabicycle[3.1.0]hexane core in a single step. To date, the acyclic carbon backbone has been synthesized in 6 steps (52-92% yield) and [3+2]azide alkene cycloaddition studies are ongoing. Anticipated future research includes completing the synthesis scheme and increasing the efficiency of specific individual steps.


Wednesday April 22, 2015 12:40pm - 1:00pm PDT
123 Zeis Hall