Tetrahedron letters

Synthesis of a novel, conformationally restricted analog of tryptophan

L Franceschetti, A Garzon-Aburbeh, MR Mahmoud…

Index: Franceschetti, Luca; Garzon-Aburbeh, Aaron; Mahmoud, Mahmoud R.; Natalini, Benedetto; Pelliciari, Roberto Tetrahedron Letters, 1993 , vol. 34, # 19 p. 3185 - 3188

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Citation Number: 15

Abstract

Abstract The synthesis of a new, conformationally restrained analog of tryptophan, 1, 2, 3, 4- tetrahydro-2-amino-2-carboxy-cyclopent [b] indole (5) is described. The key step involves the BF 3· Et 2 O Catalyzed intramolecular cyclization of α-diazoketone 2b into the 1, 2, 3, 4- tetrahydro-cyclopent [b] indol-2-one (3).