Totalsynthese des Mucronins B

Introduction of chiral 2-(aminoalkyl) substituents into 5-amino-1,3-oxazol-4-ylphosphonic acid derivatives and their use in phosphonodipeptide synthesis

“…23 As an example, the cores of the natural macrocyclic peptides mucronine B and chlamydocin were constructed by this strategy. 24,25 A recently reported route to phosphonoglycine peptidomimetics involves the formation of 2-aminoalkyl-5-amino-1,3-oxazol-4-ylphosphonic acids followed by acid cleavage of the oxazole ring. 26,27 The method is advantageous because of easily accessible and cheap starting materials as well as for high yields and facile isolation of products in each reaction step.…”

A Novel Synthetic Approach to Phosphorylated Peptidomimetics

“…Another approach is based on the reaction of glyoxylic acid derivatives with N ‐benzylurethane, which leads to N ‐benzyloxycarbonyl‐2‐ethoxyglycine derivatives. These products, when treated with phosphorus trichloride and triethyl phosphite, afford the corresponding N ‐benzyloxycarbonyl‐substituted phosphorylated glycines, which, on debenzylation with hydrogen on palladium, are applied to peptide synthesis (see, for instance, the preparation of mucronine B and chlamydocin ).…”