Formal Synthesis of 3-Deoxy-D-manno-Octulosonic Acid (KDO) and 3-Deoxy-D-arabino-2-heptulosonic Acid (DAH)

Abstract

Practical synthetic routes to 3-deoxy-D-manno-octulo-sonic acid (KDO) and 3-deoxy-D-arabino-2-heptulosonic acid (DAH) from common sugar substrates are reported. Chain homologation of the sugar substrates was accomplished by Wittig olefination and Corey-Fuchs alkynylation. A new cyclization strategy was investigated to access the desired pyranosyl isomer of the KDO target.