title: Exploring the Chemistry of Bicyclic Isoxazolidines for the Multicomponent Synthesis of Glycomimetic Building Blocks.
abstract: Starting from a chiral furanone, the nitrone-olefin [3 + 2] cycloaddition can be used to obtain bicyclic isoxazolidines for which we report a set of reactions to selectively modify each functional position. These synthetically versatile bicyclic isoxazolidines allowed us to obtain complex glycomimetic building blocks, like iminosugars, via multicomponent chemistry. For example, a library of 20 pipecolic acid derivatives, a recurring motif in various prescription drugs, could be obtained via a one-pot Staudinger/aza-Wittig/Ugi three-component reaction of a bicyclic isoxazolidine-derived azido-hemiacetal. Notably, specific pipecolic acids in this library were obtained via hydrolysis of an unique tricyclic imidate side product of the Ugi reaction. The azido-hemiacetal was also converted into an aza-C-glycoside iminosugar via an unprecendented one-pot Staudinger/aza-Wittig/Mannich reaction.
authors: Laboratory of Organic Chemistry, Wageningen University , Stippeneng 4, 6708 WE Wageningen, The Netherlands.
authors: Jorin
authors: J
authors: Hoogenboom
authors: Martin
authors: M
authors: Lutz
authors: Laboratory of Organic Chemistry, Wageningen University , Stippeneng 4, 6708 WE Wageningen, The Netherlands.
authors: Han
authors: H
authors: Zuilhof
authors: Laboratory of Organic Chemistry, Wageningen University , Stippeneng 4, 6708 WE Wageningen, The Netherlands.
authors: Tom
authors: T
authors: Wennekes