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  • Title: Scaffold diversity through intramolecular cascade reactions of solid-supported cyclic N-acyliminium intermediates.
    Author: Le Quement ST, Nielsen TE, Meldal M.
    Journal: J Comb Chem; 2007; 9(6):1060-72. PubMed ID: 17994787.
    Abstract:
    The solid-phase synthesis of pharmacologically interesting heterocycles is presented. The formation of a series of (5,5)-, (5,6)-, (6,5)-, and (6,6)-fused bicyclic ring systems was systematically studied by implementation of a common strategy involving N-acyliminium intermediates. These are highly reactive and transformed further in intramolecular cascade reactions with strong as well as weak C, N, S, and O-nucleophiles. The methodology was successfully applied to the conversion of peptidomimetics into constrained small molecule core structures, such as the hexahydropyrrolo[2,1- b][1,3]oxazines, generally with full control of diastereoselectivity (>20:1) and in purities above 90%.
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