Poster Session - Abstract # 30

Synthesis of Novel Macrocyclic N-Acyl Sulfamide Analogs Using a Build-Couple-Pair Strategy

Dimuthu A. Vithanage, Alec Lininger, and Paul R. Hanson

 Department of Chemistry, University of Kansas, Lawrence, KS, USA

A Build-Couple-Pair method to synthesize S-containing macrocycles, in particular macrocyclic N-acyl sulfamides, is reported.  The key reactions in this approach, we term “Click, Click, Cyclize,” involve constructing amine and alcohol components bearing alkene and alkyne moieties (Build phase), with subsequent condensation of each fragment to form a versatile N-acyl sulfamide linchpin (Click, Click/Couple).  Subsequent intramolecular cyclization employing either ring-closing metathesis (RCM) or ring-closing enyne metathesis (RCEM) (Cyclize/Pair) affords macrocyclic sulfamoyl carbamates.