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NHC-mediated cross-coupling of sugar-derived cyclic nitrones with enals: general and efficient synthesis of polyhydroxylated pyrrolizidines and indolizidines.

Authors
  • Xu, Wen-Yuan
  • Iwaki, Ren
  • Jia, Yue-Mei
  • Zhang, Wei
  • Kato, Atsushi
  • Yu, Chu-Yi
Type
Published Article
Journal
Organic & Biomolecular Chemistry
Publisher
The Royal Society of Chemistry
Publication Date
Jul 28, 2013
Volume
11
Issue
28
Pages
4622–4639
Identifiers
DOI: 10.1039/c3ob40696b
PMID: 23749268
Source
Medline
License
Unknown

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.

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