title: Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds.
abstract: 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.
authors.affiliation: School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
authors.forename: Jui Thiang Brian
authors.initials: JT
authors.lastname: Kueh
authors.forename: Ka Wai
authors.initials: KW
authors.lastname: Choi
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003300:Copper / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D001688:Biological Products; D013141:Spiro Compounds; D014230:Triazoles; D002244:Carbon; D003300:Copper