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  • Title: A novel one-pot approach of hexahydropyrrolo[2,3-b]indole nucleus by a cascade addition/cyclization strategy: synthesis of (+/-)-esermethole.
    Author: Lucarini S, Bartoccini F, Battistoni F, Diamantini G, Piersanti G, Righi M, Spadoni G.
    Journal: Org Lett; 2010 Sep 03; 12(17):3844-7. PubMed ID: 20795744.
    Abstract:
    A practical and efficient synthesis of 3-substituted hexahydropyrrolo[2,3-b]indole is described. The addition/cyclization of 3-substituted indoles with alpha,beta-dehydroamino esters in the presence of a Lewis acid provides hexahydropyrrolo[2,3-b]indole adducts in good yields and stereoselectivities. This approach has been applied to the concise synthesis of esermethole employing an appropriately substituted indole and an N-acyl dehydroamino ester.
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