Synthesis of macrocyclic polyhydroxy tetralactams derived from L-tartaric acid and β-hydroxyglutaric acid

✍ Scribed by Nathalie Arnaud; Claude Picard; Louis Cazaux; Pierre Tisnès

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 956 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00896-x

✦ Synopsis

The synthesis of new 16-, 18-, 19-or 20-membered secondary tetralactams with L-tartaric acid or 13-hydroxyglutaric acid moieties is investigated. The stepwise synthesis with an intermediate diamide diamine provides overall good yields (30-55%) compared with other processes using an intermediate diamide diacid or direct macrocyclization. This synthetic pathway leads to symmetrical or unsymmetrical polyhydroxytetralactams with variable hydroxyl group number. Use of mild acylating agents in this approach allows to avoid the protection-deprotection steps of hydroxyl groups.