![Synthesis of the Ficellomycin Core using a Late-Stage [3+2]-azide Alkene Cycloaddition](/media/cover_images/09b8d6be-3bf7-4d16-8cfd-15b685db86a0.jpg)
Abstract
Antibiotics are crucial for fighting bacterial infections, and many antibiotics are produced by bacteria themselves in an effort to destroy their competition. 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 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. Synthesis of the acyclic carbon backbone has been completed in 6 steps (51-91% yield) and [3+2]azide alkene cycloaddition studies are presented herein.
How to Cite
Robinson, K. R., (2015) “Synthesis of the Ficellomycin Core using a Late-Stage [3+2]-azide Alkene Cycloaddition”, Capstone, The UNC Asheville Journal of Undergraduate Scholarship 28(1).
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