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  • Title: Mechanistic insights into the stereocontrolled synthesis of hexahydropyrrolo[2,3-b]indoles by electrophilic activation of tryptophan derivatives.
    Author: López CS, Pérez-Balado C, Rodríguez-Graña P, de Lera AR.
    Journal: Org Lett; 2008 Jan 03; 10(1):77-80. PubMed ID: 18069844.
    Abstract:
    A three-step mechanism involving the formation and rearrangement of an intermediate with indoline-azetidine spirocyclic core structure was shown by DFT computations to account for the electrophilic cyclization of tryptophan derivatives to hexahydropyrrolo[2,3-b]indoles. The corresponding 3a-bromo derivatives have been obtained in high yields and synthetically useful exo/endo ratios.
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