SYNTHESIS OF MACROCYCLIC POLYHYDROXY TETRALACTAMS DERIVED FROM L-TARTARIC ACID AND BETA-HYDROXYGLUTARIC ACID

The synthesis of new 16-, 18-, 19- or 20-membered secondary tetralacta ms with L-tartaric acid or beta-hydroxyglutaric acid moieties is inves tigated. The stepwise synthesis with an intermediate diamide diamine p rovides overall good yields (30-55%) compared with other processes usi ng an intermediate diamide diacid or direct macrocyclization. This syn thetic pathway leads to symmetrical or unsymmetrical polyhydroxytetral actams with variable hydroxyl group number. Use of mild acylating agen ts in this approach allows to avoid the protection-deprotection steps of hydroxyl groups. (C) 1997 Elsevier Science.