Alkylidenecarbene insertion at anomeric C-H bonds. Synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-manno-2-octulosonic acid (KDO)

摘要

A novel method for the homologation of glycals to the corresponding 3-deoxy-2-ulosonic acids, based on the [1,5]-C-H bond insertion of alkylidenecarbenes, is presented. The application of this approach is illustrated through the synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-manno-2-octulosonic acid (KDO).