1078697-20-7Relevant academic research and scientific papers
Synthesis of spiroacetal-triazoles as privileged natural product-like scaffolds using click chemistry
Choi, Ka Wai,Brimble, Margaret A.
experimental part, p. 3518 - 3526 (2009/02/05)
The elaboration of a 6,6-spiroacetal scaffold to incorporate a triazole unit as a peptide bond surrogate at the anomeric position is described. The novel spiroacetal-triazole hybrid structures were generated via cycloaddition of a spiroacetal azide to a series of alkynes. The spiroacetal framework was constructed via Barbier reaction of bromide 10 with Weinreb amide 11, followed by acid-catalysed deprotection and cyclisation to afford the 6,6-spiroacetal ring system. The resultant ethoxy-spiroacetal 8 was converted to spiroacetal azide 5, which was then elaborated into a series of spiroacetal-triazole derivatives 7.
