Synthesis of spiroacetal-triazoles as privileged natural product-like scaffolds using "click chemistry".
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.
Choi
Ka Wai
KW
Department of Chemistry, The University of Auckland, 23 Symonds St, Auckland, New Zealand.
Brimble
Margaret A
MA
D001386:Azides / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D001386:Azides; D001688:Biological Products; D004987:Ethers; D013141:Spiro Compounds; D014230:Triazoles