848927-72-0Relevant academic research and scientific papers
Synthetic evaluation of an enantiopure tetrahydropyridine N-oxide. Synthesis of (+)-febrifugine
Ashoorzadeh, Amir,Archibald, Glenn,Caprio, Vittorio
experimental part, p. 4671 - 4680 (2009/10/09)
A study into the synthesis and synthetic utility of (S)-3-benzyloxy-3,4,5,6-tetrahydropyridine N-oxide is described. This nitrone is readily accessed from l-glutamic acid and the regio- and stereoselectivity of cycloaddition of this compound with a range
A convergent enantioselective synthesis of the anti-malarial agent (+)-febrifugine
Ashoorzadeh, Amir,Caprio, Vittorio
, p. 346 - 348 (2007/10/03)
Chiral pool derived 3-benzyloxy-3,4,5,6-tetrahydropyridine N-oxide underwent regio- and diastereoselective 1,3-dipolar cycloaddition with N-allylquinazolone to give a cycloadduct that was elaborated to (+)-febrifugine a potent anti-malarial alkaloid.
Catalytic asymmetric synthesis of febrifugine and isofebrifugine
Kobayashi, Shu,Ueno, Masaharu,Suzuki, Ritsu,Ishitani, Haruro
, p. 2175 - 2178 (2007/10/03)
Antimalarial alkaloids, febrifugine (1) and isofebrifugine (2), were synthesized from simple achiral starting materials using tin(II)-catalyzed catalytic asymmetric aldol reaction and lanthanide-catalyzed aqueous three- component reaction as the key steps. These unambigous total syntheses revealed that the absolute configurations of febrifugine and isofebrifugine were not (2'S, 3'R) and (2'R, 3'R) as reported previously but (2'R, 3'S) and (2'S, 3'S), respectively.
