Here, we demonstrate the applicability of the 2,5-dimethylpyrrolo unit as a complementary N-protecting group in the highly diastereoselective synthesis of more than 20 different anti-amino alcohols (63-90% yield with up to 20:1 dr). Cleavage of the pyrrolo-N-protecting group was accomplished e.g. in the presence of NH2OH under microwave conditions with yields exceeding 80%. The applicability of the protecting groups was further demostrated by the shortest yet reported total synthesis of the sphinganine-like natural product clavaminol A. The application of the N-pyrrolo protecting group also offers the possibility analyse product micxtures by NMR measurements due to the absence of conformational isomers, which are otherwise common for N-protecting groups.