Synthesis of a Metabolite of an Anti-Angiogenic Lead Candidate Based on a D-Glucosamine Motif

A rapid synthetic access to ACL 21269 was established in 12 steps starting from thiogylcoside 9 utilizing synthons 8 and 6 to introduce the pharmacophores at positions 1 and 2. The functional groups decorating the glucosamine scaffold were introduced in a particular order and common protecting groups were employed to establish a robust synthetic process. (C) 2008 Elsevier Ltd. All rights reserved.