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Title: Facile synthesis of 12-carboxamido-11-spirostenes via palladium-catalyzed carbonylation reactions
Authors: Ács, Péter 
Müller, Erno 
Czira, Gábor 
Mahó, Sándor 
Perreira, Mariette 
Kollár, László 
Keywords: Iodo-alkenene; Carboxamide; Hecogenin; Palladium-catalyst; Carbonylation
Issue Date: 2006
Citation: Steroids. 71:10 (2006) 875-879
Abstract: 12-Carboxamido- and 12-carboxyl-11-spirostenes were synthesized from the corresponding 12-iodo-11-ene derivative in palladium-catalyzed carbonylation reactions under mild reaction conditions. The synthesis of the iodo-alkene substrate is based on the transformation of the 12-keto derivative (hecogenin) to hydrazone, which was treated with iodine in the presence of a base (1,1,3,3-tetramethyl guanidine). While various 12-carboxamides were synthesized in moderate to high yields by using simple alkyl/arylamines or amino acid methylesters as N-nucleophiles, low yields can be achieved with alcohols as O-nucleophiles. The homogeneous carbonylation reactions tolerate the 3-hydroxy substituent and the spiroacetal moiety.
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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