Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 28, Pages 4622-4639Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob40696b
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Funding
- National Basic Research Program of China [2011CB808603, 2012CB822101]
- The Natural Science Foundation of China [21272240]
- Chinese Academy of Sciences
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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, gamma-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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