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A general solid phase methodology for the synthesis of depside and depsipeptide chains from optically active α-hydroxy acids and α-amino acids is reported. The automated preparation of depsides (97% yield per cycle) made up from the same enantiomer [i.e. H-[(S)-Man] 8 -OH, 1], by both enantiomers [i.e. H-[(R)-Man-(S)-Man] 4 -OH, 2], or by different hydroxy acids in the same chain...