Tetrahedron: Asymmetry

Straightforward chemo-enzymatic synthesis of new aminocyclitols, analogues of valiolamine and their evaluation as glycosidase inhibitors

L El Blidi, M Ahbala, J Bolte, M Lemaire

Index: El Blidi, Lahssen; Ahbala, Mustapha; Bolte, Jean; Lemaire, Marielle Tetrahedron Asymmetry, 2006 , vol. 17, # 18 p. 2684 - 2688

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Citation Number: 39

Abstract

An efficient fructose-1, 6-bisphosphate aldolase mediated synthesis of new aminocyclitol analogues of valiolamine is described. The one-pot process where four stereocentres are created involves the formation of two carbon–carbon bonds. One is catalysed by the aldolase, coupling dihydroxyacetone phosphate to nitrobutyraldehydes. The other is the result of a highly stereoselective intramolecular Henry reaction occurring on the ...