Synthesis of iminosugars via 1,3-dipolar cycloaddition reactions of nitrones to α,β-unsaturated sugar aldonolactones

Synthesis of Polyhydroxylated Quinolizidine and Indolizidine Scaffolds from Sugar-Derived Lactams via a One-Pot Reduction/Mannich/Michael Sequence

“…On the basis of our previous experience, we focused our attention on sugar-derived nitrones as imine precursors. For this purpose the pentose-derived nitrones 5a , b − were prepared according to literature protocols.…”

A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides

“…During the last decade, Chmielewski’s group has continued its investigation on 1,3-dipolar cycloaddition of nitrones to carbohydrate derived δ-lactones, e.g., 101 . Their research has proven useful from theoretical and practical standpoints, and some of the resulting cycloaddition adducts have been applied to the synthesis of biologically relevant iminosugars [119].…”

Synthesis of Polyhydroxylated Piperidine and Pyrrolidine Peptidomimetics via One-Pot Sequential Lactam Reduction/Joullié–Ugi Reaction

“…The reported bioactivity of compounds of types 1 – 3 as well as our long-term interest in the stereocontrolled synthesis of bioactive compounds, such as β-lactams, iminosugars, and alkaloids, prompted us to search for an attractive method of the synthesis of such polyhydroxylated cyclic amino amides.…”