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  • Title: Organocatalytic enantioselective formal synthesis of bromopyrrole alkaloids via aza-Michael addition.
    Author: Lee SJ, Youn SH, Cho CW.
    Journal: Org Biomol Chem; 2011 Oct 26; 9(22):7734-41. PubMed ID: 21952717.
    Abstract:
    An unprecedented organocatalytic enantioselective formal synthesis of bromopyrrole alkaloid natural products is reported. An organocatalytic aza-Michael addition using pyrroles as the N-centered nucleophile is utilized as the enantioselective step to construct the nitrogen-substituted stereogenic carbon center in bromopyrrole alkaloids in good yield and excellent enantioselectivity. The aza-Michael product is converted via lactamization using a Staudinger-type reductive cyclization to the key intermediate, which was previously used in the total synthesis of bromopyrrole alkaloid natural products.
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