A practical and efficient synthesis of 3-substituted hexahydropyrrolo[2,3-b]indole is described. The addition/cyclization of 3-substituted indoles with alfa,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.
A Novel One-Pot Approach of Hexahydropyrrolo[2,3-b]indole Nucleus by a cascade addition/cyclization strategy: Synthesis of (±)-Esermethole
LUCARINI, SIMONE;BARTOCCINI, FRANCESCA;DIAMANTINI, GIUSEPPE;PIERSANTI, GIOVANNI;SPADONI, GILBERTO
2010
Abstract
A practical and efficient synthesis of 3-substituted hexahydropyrrolo[2,3-b]indole is described. The addition/cyclization of 3-substituted indoles with alfa,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.File in questo prodotto:
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