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Synthetic scheme for generating N5-(1-iminoalk(en)yl)-l-ornithine derivatives. Reagents and Conditions: (i) dry HCl(g) at 0 °C for 1 h, stop HCl(g), then 0 °C for 4 h and RT overnight; (ii) H2O, 5 °C, pH = 10, 1.5 h, adjust pH = 7, overnight, Dowex 50WX8-400 (H2O then 10% aqueous pyridine); (iii) 6 M HCl, EtOAc, 84%–94% from Nα-Boc-l-ornithine (52). Adapted with permission from [127]. Copyright 1999 American Chemical Society.
