Approaches to the world's smallest and tightest knot

ORGN 559

Edward E. Fenlon, edward.fenlon@fandm.edu and Brandon Ito, bito@fandm.edu. Department of Chemistry, Franklin & Marshall College, PO Box 3003, Lancaster, PA 17604
Progress towards the “thread and cut” synthesis of a trefoil knot containing only 72 atoms in its backbone will be presented. The eight-step synthetic route involves Etherifications and an azide-alkyne Click-cycloaddition step for the knot precursor (Figure). A Ring-closing metathesis reaction is used for tying the knot followed by ester hydrolysis (the "cut" step), leading to what we term ECR knots. Use of NMR chiral shift reagents for characterization will also be discussed.