Transformation of 5‐Hydroxy‐ to (5‐Chloropentanoyl)amino Derivatives under ‘Direct Amide Cyclization’ Conditions

The application of the ‘direct amide cyclization’ conditions to the linear δ‐hydroxy diamide 11 is described (Scheme 3). Instead of the cyclization to the expected nine‐membered cyclodepsipeptide, only the chloro acid 12 was obtained. Its formation could be explained by consecutive formation of the 1,3‐oxazol‐5(4H)‐one 16 and the six‐membered imino lactone 17 as intermediates (Scheme 4). The spontaneous isomerization of the latter gave 12 in a good yield.