Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffoldsElectronic supplementary information (ESI) available: Experimental details and characterisation data for compounds 11, 17-19, 23-26, azides 27a-h, and spiroacetal-triazoles 28a-h and 10a-h. 1H and 13C NMR spectra of all new compounds. See DOI: 10.1039/c2ob06802hThis article is part of the Organic & Biomolecular Chemistry 10th Anniversary issue

• Main Authors: Kueh, Jui Thiang Brian, Choi, Ka Wai, Brimble, Margaret A
• Format: Article
• Language: English
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c2ob06802h

The enantioselective synthesis of novel C -linked spiroacetal-triazoles 10 is reported. The key step involves reaction of acetylenic spiroacetal 11 with several azides by the Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold 11 was prepared from silyl-protected Weinreb amide 19 using several reliable Grignard additions and a highly diastereoselective enzymatic kinetic resolution. The union of the biologically privileged 6,6-spiroacetal scaffold with azides by the regioselective Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC) affords novel C -linked spiroacetal-triazoles. The anomeric C -linkage is anticipated to provide increased stability towards hydrolytic cleavage.