1233083-99-2Relevant academic research and scientific papers
Total synthesis of pseudacyclins A–E by an on-resin head-to-side chain concomitant cyclization-cleavage reaction
Bérubé, Christopher,Borgia, Alexandre,Voyer, Normand
, p. 4176 - 4179 (2018)
Taking advantage of the nucleophile-sensitive ester link of oxime resin, a novel synthetic strategy was applied to the first synthesis of a type of cyclic peptides known as pseudacyclins A–E. The endocyclic ornithine side-chain part was incorporated by an on-resin acid-catalyzed concomitant cyclization-cleavage reaction after a selective deprotection of orthogonally protected ornithine. The synthetic methodology gives high macrocyclization yields and low oligomerization side-products. The combination used of solid-phase/solution-phase strategy was efficient to prepare pseudacyclins and could prove useful to prepare other natural cycle-tail peptides.
