Stereoselective syntheses of 1,4-dideoxy-1,4-imino-octitols and novel tetrahydroxyindolizidines

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dc.contributor.author Carmona, A. T.
dc.contributor.author Fuentes, Jose M.
dc.contributor.author Winters, Ana L.
dc.contributor.author Vogel, P.
dc.contributor.author Robina, I.
dc.contributor.author Garcia, E. R.
dc.contributor.author Demange, R.
dc.date.accessioned 2010-03-04T15:38:08Z
dc.date.available 2010-03-04T15:38:08Z
dc.date.issued 2003-04-24
dc.identifier.citation Carmona , A T , Fuentes , J M , Winters , A L , Vogel , P , Robina , I , Garcia , E R & Demange , R 2003 , ' Stereoselective syntheses of 1,4-dideoxy-1,4-imino-octitols and novel tetrahydroxyindolizidines ' Journal of Organic Chemistry , pp. 3874-3883 . , 10.1021/jo026688a en
dc.identifier.issn 0022-3263
dc.identifier.other PURE: 137302
dc.identifier.other dspace: 2160/4167
dc.identifier.uri http://hdl.handle.net/2160/4167
dc.description Carmona, A. T., Fuentes, J., Robina, I., Garcia, E. R., Demange, R., Vogel, P., Winters, A. L. (2003). Stereoselective syntheses of 1,4-dideoxy-1,4-imino-octitols and novel tetrahydroxyindolizidines.  Journal of Organic Chemistry, 68, (10), 3874-3883. Sponsorship: European COST Program, working groups COST-D13-0001/98 and D25-0001/02. en
dc.description.abstract A new route for the preparation of four new indolizidines, (1R,2S,6S,7S,8aS)- and (1R,2S,6R,7R,8aS)-1,2,6,7-tetrahydroxyindolizidine and (1S,2R,7S,8S,8aR)- and (1S,2R,7R,8R,8aR)-1,2,7,8-tetrahydroxyindolizidine is reported. The synthesis is based on Knoevenagel homologation of the readily available enantiomerically pure pyrrolidin-carbaldehydes 13 and 37 followed by asymmetric dihydroxylation of the subsequent alkenyl pyrrolidines and cyclization of the corresponding imino-octitols. The new indolizidines and their precursors (imino-octitols 20, 25, 26) and indolizidinones 28a and 28b have been tested for inhibitory activities toward 26 glycosidases. The enzymatic inhibition of trans-7-hydroxy-d-(−)-swainsonine toward α-mannosidases is similar to that described for trans-7-hydroxy-l-(+)-swainsonine (11b) toward naringinase (α-l-rhamnosidase from Penicillium decumbens). en
dc.format.extent 10 en
dc.language.iso eng
dc.relation.ispartof Journal of Organic Chemistry en
dc.title Stereoselective syntheses of 1,4-dideoxy-1,4-imino-octitols and novel tetrahydroxyindolizidines en
dc.type Text en
dc.type.publicationtype Article (Journal) en
dc.identifier.doi http://dx.doi.org/10.1021/jo026688a
dc.contributor.institution Institute of Biological, Environmental and Rural Sciences en
dc.description.status Peer reviewed en


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