55893-12-4Relevant academic research and scientific papers
Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
Nemoto, Tetsuhiro,Yamaguchi, Mami,Kakugawa, Kazumi,Harada, Shingo,Hamada, Yasumasa
, p. 2547 - 2555 (2015)
Gephyrotoxin 287C, a bioactive alkaloid bearing a perhydropyrrolo[1,2-a]quinoline skeleton with five stereocenters, is an attractive target for synthetic organic chemistry. We achieved an enantioselective total synthesis of (+)-gephyrotoxin 287C, for which the key steps were palladium-catalyzed asymmetric allylic amination using a chiral diaminophosphine oxide (DIAPHOX) preligand, diastereoselective intramolecular Mannich reaction, and tin tetrachloride-catalyzed diastereoselective conjugate addition/protonation.
Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
Piccichè, Miriam,Pinto, Alexandre,Griera, Rosa,Bosch, Joan,Amat, Mercedes
, p. 6654 - 6657 (2017)
A synthesis of (+)-gephyrotoxin 287C using (S)-phenylglycinol-derived tricyclic lactam 7 as the starting enantiomeric scaffold is reported. From the stereochemical standpoint, the key steps are the generation of the DHQ C-5 stereocenter by hydrogenation of the C-C double bond, removal of the chiral inductor to give a cis-DHQ, introduction of the DHQ C-2 substituent, completion of the (Z)-enyne moiety, and generation of the C-1 stereocenter during closure of the pyrrolidine ring.
