A Novel One-Pot Approach of Hexahydropyrrolo[2,3-b]indole Nucleus by a cascade addition/cyclization strategy: Synthesis of (±)-Esermethole
Organic Letters2010Vol. 12(17), pp. 3844–3847
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Simone Lucarini, Francesca Bartoccini, Flavia Battistoni, Giuseppe Diamantini, Giovanni Piersanti, Marika Righi, Gilberto Spadoni
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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