Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases. Issue 2 (8th January 2015)

• Record Type: Journal Article
• Authors: Minehira, Daisuke; Okada, Takuya; Iwaki, Ren; Kato, Atsushi; Adachi, Isao; Toyooka, Naoki
• Is Part Of: Tetrahedron letters. Volume 56:Issue 2(2015)
• Page Start: 331
• Page End: 334
• Publication Date: 2015-01-08
• Subjects: Imino sugar -- Pyrrolizidine -- Hyacinthacine -- Enantiodivergent strategy -- Glycosidase; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2014.11.087
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The enantiodivergent synthesis of polyhydroxylated pyrrolizidines has been achieved, starting from common intermediate 1 . The synthesis involved the stereoselective construction of the pyrrolizidine core unit by using intramolecular Michael cyclization reaction as the key reaction. The synthesized eight isomers were evaluated for various glycosidase inhibition effects. Compound 15 showed a moderate inhibitory activity against α-l -fucosidase and a high selectivity compared from the other glycosidases.