title: Solid phase versus solution phase synthesis of  heterocyclic macrocycles.
abstract: Comparing a solution phase route to a solid phase route in the synthesis of the cytotoxic natural product urukthapelstatin A (Ustat A) confirmed that a solid phase method is superior. The solution phase approach was tedious and involved cyclization of a ridged heterocyclic precursor, while solid phase allowed the rapid generation of a flexible linear peptide. Cyclization of the linear peptide was facile and subsequent generation of three oxazoles located within the structure of Ustat A proved relatively straightforward. Given the ease with which the oxazole Ustat A precursor is formed via our solid phase approach, this route is amenable to rapid analog synthesis.
authors: School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia.
authors: Seong Jong
authors: SJ
authors: Kim
authors: Shelli R
authors: SR
authors: McAlpine
mesh_terms: D003500:Cyclization; D003545:Cysteine / Q000737:chemistry; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D012694:Serine / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques; D012996:Solutions; D013844:Thiazoles / Q000138:chemical synthesis*
chemical_list: D010456:Peptides, Cyclic; D012996:Solutions; D013844:Thiazoles; C521435:urukthapelstatin A; D012694:Serine; D007930:Leucine; D003545:Cysteine