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A formal synthesis of (±)-physostigmine via 3,3-rearrangement of a bis-enamine
Authors:Paulo F. Santos  Paulo S. Almeida  Sundaresan Prabhakar
Affiliation:a Chemistry Department, Centro de Química, University of Trás-os-Montes and Alto Douro, Apartado 202, 5001-911 Vila Real, Portugal
b Chemistry Department, REQUIMTE/CQFB, Campus Faculty of Sciences and Technology, New University of Lisbon, and SINTOR-UNINOVA, 2829-516 Monte de Caparica, Portugal
c Chemistry Department, Unidade I&D de Materiais Téxteis e Papeleiros, University of Beira Interior, 6201-001 Covilhã, Portugal
Abstract:A new flexible approach to hexahydropyrrolo[2,3-b]indole system via the [3,3]-sigmatropic rearrangement of 1-(2′-methoxycarbonyl-N-methylvinylamino)skatole, culminating in the synthesis of (±)-desoxyeseroline, is described.
Keywords:Physostigmine   Eseroline   Enamines   Sigmatropic rearrangements
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