Routes to putative N-acyl-d-ala-d-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω- aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to ...
[Dawadi, Prativa B. S.; Schulten, Els A. M.; Lugtenburg, Johan Journal of Labelled Compounds and Radiopharmaceuticals, 2009 , vol. 52, # 9 p. 341 - 349]