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Synlett 2000; 2000(6): 0874-0876
DOI: 10.1055/s-2000-6703
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Straightforward Access to [6]Metacyclophene-based Enynes by an Inter-Intramolecular Tandem Etherification through a One-Pot Double SNAr Reaction

Jean Suffert* , Stéphane Raeppel, Franck Raeppel, Bruno Didier
  • *Laboratoire de Pharmacochimie de la Communication Cellulaire, Université Louis Pasteur de Strasbourg, Faculté de Pharmacie, UMR 7081 du CNRS, 74, route du Rhin, BP 24, F-67401 Illkirch Cedex, France; Fax (33) 3 88 67 47 94; E-mail: jeansu@pharma.u-strasbg.fr
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Publication Date:
31 December 2000 (online)

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The first application in the enediyne area of an inter-intramolecular tandem one-pot double SNAr reaction is demonstrated towards the synthesis of new bi- and tricyclic enediynes 1 and 17, respectively. These polyunsaturated macrocycles are very stable and are not prone to rearrange to a diradical species via a Bergman cycloaromatization. The 1,3-substitution pattern on the aromatic ring could impede this thermal process from occurring.

macrocyclic enediynes - macrocyclization - SNAr reaction

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