A versatile route to functionalized dilactones as monomers for the synthesis of poly(α-hydroxy) acids

Article abstract of DOI:10.1002/ejoc.200300181

A synthetic pathway to functionalized six-membered dilactones structurally analogous to lactide is described. Through the use of orthogonal protecting groups, the synthesis of functionalized dilactones was performed in a straightforward way by cyanuric chloride-mediated cyclization of the corresponding linear α-hydroxy acid dimers. The synthesis of three different dilactones - methylglycolide, benzyloxymethylglycolide, and 2-benzyloxymethyl-5-methylglycolide - by the same procedure demonstrated the versatility of this route. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.