Kaliappan, Krishna P. ; Das, Prasanta ; Chavan, Sanjay T. ; Sabharwal, Sushma G. (2009) A versatile access to calystegine analogues as potential glycosidases inhibitors The Journal of Organic Chemistry, 74 (16). pp. 6266-6274. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo901342w
Related URL: http://dx.doi.org/10.1021/jo901342w
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 α-mannosidase and N-acetyl-β-D-glucosaminidase.
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 104975 |
Deposited On: | 19 May 2017 10:25 |
Last Modified: | 19 May 2017 10:25 |
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