Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative

Article abstract of DOI:10.1021/jo00127a047

The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a non-carbohydrate precursor was achieved in six steps (19percent yield) from a chiral, γ,δ-epoxy β-hydroxy ester, 3a, readily available from the corresponding α,β-epoxy aldehyde.The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.