Practical synthesis of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) |
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Authors: | Crich David Navuluri Chandrasekhar |
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Institution: | Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA. DCrich@chem.wayne.edu |
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Abstract: | Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the α-keto acid moiety from the alkyne. |
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