Formal synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via desymmetrization by ring-closing metathesis.
[figure: see text] Formal synthesis of the naturally occurring deaminated sialic acid KDN, a potential oncofetal antigen, has been accomplished in 45% overall yield via a novel ketalization/ring-closing metathesis sequence. The rapid introduction of all oxygen functionality in a completely stereocontrolled manner exploited a rigid 6,8-dioxabicyclo[3.2.1]oct-2-ene ring system. This general synthetic strategy should provide access to a number of KDN and sialic acid analogues.
Burke
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SD
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1396, USA. burke@chem.wisc.edu
Voight
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EA
D002236:Carbohydrate Conformation; D007202:Indicators and Reagents; D008958:Models, Molecular; D013237:Stereoisomerism; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D013400:Sugar Acids; C050008:3-deoxyglycero-galacto-nonulosonic acid