Choi Ka Wai, Brimble Margaret A
Department of Chemistry, The University of Auckland, 23 Symonds St, Auckland, New Zealand.
Org Biomol Chem. 2008 Oct 7;6(19):3518-26. doi: 10.1039/b808454h. Epub 2008 Aug 5.
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.
本文描述了一种6,6-螺缩醛支架的构建，该支架在异头位置引入了一个三唑单元作为肽键替代物。新型螺缩醛-三唑杂化结构是通过螺缩醛叠氮化物与一系列炔烃的环加成反应生成的。螺缩醛骨架是通过溴化物10与Weinreb酰胺11的Barbier反应构建的，随后进行酸催化脱保护和环化反应，得到6,6-螺缩醛环系统。所得的乙氧基-螺缩醛8转化为螺缩醛叠氮化物5，然后将其进一步转化为一系列螺缩醛-三唑衍生物7。
