Synthesis of 8-homocastanospermine

Paśniczek, Konrad; Socha, Dariusz; Jurczak, Margarita; Solecka, Jolanta; Chmielewski, Marek
April 2006
Canadian Journal of Chemistry;Apr2006, Vol. 84 Issue 4, p534
Academic Journal
The 1,3-dipolar cycloaddition of a five-membered cyclic nitrone derived from malic acid (4) and unsaturated D-threo-hexaldonolactone (1) leads to a single adduct 6, which can be transformed into the 8-homocastanospermine (13) via a sequence involving rearrangement of the six-membered lactone ring into the five-membered one, removal of the terminal carbon atom from the sugar chain, cleavage of the N—O bond, and the intramolecular alkylation of the nitrogen atom. The iminosugar (13) does not show any interesting inhibitory activity towards α- and β-glucosidases.


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