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https://hdl.handle.net/10316/5072
Title: | Facile synthesis of 12-carboxamido-11-spirostenes via palladium-catalyzed carbonylation reactions | Authors: | Ács, Péter Müller, Erno Czira, Gábor Mahó, Sándor Pereira, 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. | URI: | https://hdl.handle.net/10316/5072 | DOI: | 10.1016/j.steroids.2006.05.019 | Rights: | openAccess |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais |
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file8c46c3e9907540b58a44201cd4b8237d.pdf | 217.39 kB | Adobe PDF | View/Open |
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