(+)-Lentiginosine (14) and (7R)-7-hydroxylentiginosine (26), powerful inhibitors of amyloglucosidases, and their enantiomers were obtained in high overall yields by a multistep synthesis involving 1,3-dipolar cycloaddition of enantiopure tartaric acid derived pyrroline N-oxides. Structurally related (S,S)-3,4-dihydroxypyrrolidines 29-33 were synthesized as simpler models and tested towards 24 glycosidases.
Polyhydroxypyrrolidine Glycosidase Inhibitors Related to (+)-Lentiginosine / F. Cardona; A. Goti; S. Picasso; P. Vogel; A. Brandi. - In: JOURNAL OF CARBOHYDRATE CHEMISTRY. - ISSN 0732-8303. - STAMPA. - 19:(2000), pp. 585-601. [10.1080/07328300008544101]
Polyhydroxypyrrolidine Glycosidase Inhibitors Related to (+)-Lentiginosine
CARDONA, FRANCESCA;GOTI, ANDREA;BRANDI, ALBERTO
2000
Abstract
(+)-Lentiginosine (14) and (7R)-7-hydroxylentiginosine (26), powerful inhibitors of amyloglucosidases, and their enantiomers were obtained in high overall yields by a multistep synthesis involving 1,3-dipolar cycloaddition of enantiopure tartaric acid derived pyrroline N-oxides. Structurally related (S,S)-3,4-dihydroxypyrrolidines 29-33 were synthesized as simpler models and tested towards 24 glycosidases.
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