Solid phase synthesis of enantiomerically pure polyhydroxyvalerolactams

A general method for the solid phase synthesis of type 2 3,4,5-trihydroxypiperidin-2-ones is described. Amination of d-ribonolactone 4 was accomplished using a Mitsunobu reaction, and type 7 aminolactone underwent direct lactamisation upon treatment with NaOAc. For the solid phase synthesis, the aminoacid was anchored directly to a TentaGel® resin, and the lactamisation step was concomitant with the cleavage from the resin.