35285-26-8Relevant articles and documents
Rapid configuration analysis of the solenopsins
Pianaro, Adriana,Fox, Eduardo G.P.,Bueno, Odair C.,Marsaioli, Anita J.
, p. 635 - 642 (2012/09/22)
A protocol for rapid access to the relative and absolute configurations of the solenopsins, the venom alkaloids of fire ants (Solenopsis spp.), was developed based on chiral capillary gas chromatography. The synthesis of racemic mixtures of 2-methyl-6-alkylpiperidines and the isolation of natural (2R,6R)- and (2R,6S)-2-methyl-6-undecylpiperidines allowed for the standardization of the chromatographic method. Application of this protocol revealed the previously unknown natural occurrence of four stereoisomers of 2-methyl-6-undecylpiperidine in venom samples from workers and gynes of Solenopsis saevissima.
A simple and efficient enantioselective synthesis of piperidine alkaloids dihydropinidine and isosolenopsins A, B and C
Ciblat, Stephane,Besse, Pascale,Papastergiou, Vassiliki,Veschambre, Henri,Canet, Jean-Louis,Troin, Yves
, p. 2221 - 2229 (2007/10/03)
A diastereospecific intramolecular Mannich-type reaction, involving enantiopure amine 4 and achiral aldehydes, is employed as the key step of an efficient total enantioselective synthesis of five piperidine alkaloids. Copyright (C) 2000 Elsevier Science Ltd.
Synthesis of solenopsin B via stereoselective reduction of Bicyclic N,O-ketals
Kotsuki, Hiyoshizo,Kusumi, Toshio,Inoue, Mase,Ushio, Yasuyuki,Ochi, Masamitsu
, p. 4159 - 4162 (2007/10/02)
A new enantioselective total synthesis of (-)-solenopsin B was described starting from L-glutamic acid as an optically active natural source, in which stereoselective reduction of bicyclic N,O-ketals with DIBALH was used as the key reaction step.