1089173-74-9Relevant articles and documents
Total synthesis and determination of the absolute configuration of guadinomines B and C2
Hirose, Tomoyasu,Sunazuka, Toshiaki,Tsuchiya, Satoshi,Tanaka, Toshiaki,Kojima, Yasuhiro,Mori, Ryuma,Iwatsuki, Masato,Omura, Satoshi
experimental part, p. 8220 - 8238 (2009/09/30)
This article describes the determination of the absolute configurations of the guadinomines, which are novel cyclic guanidyl natural products that are inhibitors of the type III secretion system (TTSS) of bacteria. Any compound that interrupts the TTSS of bacteria is potentially an ideal anti-infectious drug. The reliable asymmetric synthesis of guadinomines has revealed their absolute configurations, which could not have been defined without this synthetic approach. Our report not only describes the asymmetric total synthesis of the title compounds, but also demonstrates the novel concise synthesis of tri-substituted piperazinone cores as optically pure forms. The novel feature of our method is an intramolecular SN2 cyclization that uses PPh 3 and I2 to construct the unique 5membered cyclic guanidine substructure.
