title: NHC-mediated cross-coupling of sugar-derived cyclic nitrones with enals: general and efficient synthesis of polyhydroxylated pyrrolizidines and indolizidines.
abstract: A general and efficient method for the synthesis of polyhydroxylated pyrrolizidines and indolizidines has been developed based on the NHC-catalyzed cross-coupling of sugar-derived cyclic nitrones with enals, which afforded the key intermediates, γ-hydroxyl amino esters, in good to excellent yields. Thus, a variety of polyhydroxylated pyrrolizidines and indolizidines have been synthesized and assayed against various glycosidases, which showed that aryl or alkyl substituents at C-7 of pyrrolizidines or at C-8 of indolizidines reduced the potency of the glycosidase inhibition of these bicyclic iminosugars.
authors.affiliation: Beijing National Laboratory for Molecular Science (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100191, China.
authors.forename: Wen-Yuan
authors.initials: WY
authors.lastname: Xu
authors.forename: Ren
authors.initials: R
authors.lastname: Iwaki
authors.forename: Yue-Mei
authors.initials: YM
authors.lastname: Jia
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Chu-Yi
authors.initials: CY
authors.lastname: Yu
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006571:Heterocyclic Compounds / Q000737:chemistry*; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007659:Ketones / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D002241:Carbohydrates; D004791:Enzyme Inhibitors; D006571:Heterocyclic Compounds; D054836:Indolizidines; D007659:Ketones; D009589:Nitrogen Oxides; D011763:Pyrrolizidine Alkaloids; C015388:nitrones; C030011:carbene; D006026:Glycoside Hydrolases; D008697:Methane