Related Experiment Videos
Synthesis of sialic acids via desymmetrization by ring-closing metathesis
Eric A Voight1, Christian Rein, Steven D Burke
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1396, USA.
Abstract:
Formal total syntheses of the naturally occurring deaminated sialic acids KDN (2), a potential oncofetal antigen, and N-acetylneuraminic acid (Neu5Ac, 1), the most naturally abundant sialic acid, have been accomplished in 46% and 9.3% overall yield, respectively, via a novel ketalization/ring-closing metathesis sequence. The rapid introduction of all oxygen and nitrogen functionality in a completely stereocontrolled manner exploited a rigid 6,8-dioxabicyclo[3.2.1]oct-2-ene template. The 2,7-anhydro-KDN derivative 40 served as an advanced intermediate in each of the two syntheses.