Affiliation:
1. Instituto de Ciências Ambientais Químicas e Farmacêuticas Universidade Federal de São Paulo Rua Prof. Artur Riedel, 275 Diadema SP 09972-270 Brazil
2. Escola Paulista de Medicina Laboratório de Endocrinologia Translacional Universidade Federal de São Paulo Av. Pedro de Toledo, 781 São Paulo SP 04039-032 Brazil
Abstract
AbstractA dehydroaporphine intermediate obtained via benzyne chemistry was used to accomplish the enantioselective total synthesis of (S)‐nuciferine, the first total synthesis of (±)‐urabaine, and our second‐generation total synthesis of lysicamine. (S)‐Nuciferine was obtained by an unprecedented late‐stage asymmetric hydrogenation employing a chiral iridium(I) catalyst. The first total synthesis of (±)‐urabaine and the second‐generation total synthesis of lysicamine, which exhibited low cytotoxicity and neuroprotective activity, were completed by oxidation reactions in 7 and 6 steps, respectively.
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