Stereoselective synthesis of novel tetrahydroxypyrrolizidines
N-Benzyloxycarbonyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose 12a has been converted into (1R,2S,6R, 7S,7aS)-5 and (1R, 2S, 6S, 7R, 7aR)-1,2,6,7-tetrahydroxypyrrolidin-5-ones 6 and (1R,2S,6S,7S,7aS)-7 and (1R,2S,6R,7R,7aS)-1,2,6,7-tetrahydroxypyrrolizidines 8 following stereoselective paths. These new compounds have been assayed for their inhibitory activities towards 25 glycosidases. Pyrrolizidines 7 and 8 are moderate but selective inhibitors of amyloglucosidase from Rhizopus mold (7: IC50 = 130 muM, K-i = 120 muM; 8: IC50 = 200 muM, K-i = 180 muM, mixed type of inhibition). (C) 2003 Elsevier Ltd. All rights reserved.
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Keywords: pyrrolizidines ; enzymatic inhibitors ; azasugars ; enzyme inhibition ; sharpless asymmetric dihydroxylation ; pyrrolidines ; immosugars ; pyrrolizidinones ; Functionalized cyclic nitrones ; human alpha-mannosidases ; 1st ; total-synthesis ; hydroxylated pyrrolizidines ; polyhydroxylated ; pyrrolidines ; cycloaddition reactions ; closing metathesis ; part 2 ; route ; indolizidines ; pyrrolidines
Univ Sevilla, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain. Swiss Fed Inst Technol, Inst Mol & Biol Chem, BCH, EPFL, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08