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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/3698

Title: A Versatile Access to Calystegine Analogues as Potential Glycosidases Inhibitors
Authors: KALIAPPAN, KP
DAS, P
CHAVAN, ST
SABHARWAL, SG
Keywords: ring-closing metathesis
asymmetric 1,3-dipolar cycloaddition
medium-sized rings
gong-teng-a
olefin metathesis
organic-synthesis
enantiomerically pure
(+)-calystegine b-2
synthetic route
nitrones
Issue Date: 2009
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY, 74(16), 6266-6274
Abstract: An efficient metathetic strategy and nitrone chemistry have been suitably tethered to construct 8-azabicyclo[3.2.1]octanes as versatile precursors for the synthesis of several calystegine analogues. This synthetic strategy relies on the ability of mannose-derived nitrone to undergo a highly stereoselective nucleophilic addition of various Grignard reagents to access syn orientation of alkenes, which then smoothly undergo ring-closing metathesis (RCM) to provide this framework. These RCM products 18 and 20 have been successfully used as advance precursors to synthesize many calystegine analogues (27, 36, 38, 40, 43, and 44) either by syn-dihydroxylation or by hydrogenation and followed by global deprotection. Interestingly, both compounds 36 and 40 exhibited significant noncompetitive inhibition against alpha-mannosidase and N-acetyl-beta-D-glucosaminidase.
URI: http://dx.doi.org/10.1021/jo901342w
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3698
http://hdl.handle.net/10054/3698
ISSN: 0022-3263
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