496047-69-9Relevant academic research and scientific papers
A new divergent synthesis of (+)- and (-)-ferruginine utilizing PLE-catalyzed asymmetric dealkoxycarbonylation
Katoh, Takahiro,Kakiya, Kiyoshi,Nakai, Takashi,Nakamura, Soichi,Nishide, Kiyoharu,Node, Manabu
, p. 2351 - 2358 (2007/10/03)
A new divergent synthesis of (+)- and (-)-ferruginine 4, via the optically active 8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylates 6 is described. The β-keto ester intermediates 6 were prepared by a novel PLE-catalyzed asymmetric dealkoxycarbonylation of the symmetric tropinone-type diesters 5. The key problem in the synthesis is controlling the regioselectivity of the reaction at the 2- and 4-positions in the tropane framework of the β-keto ester 6 for introduction of the acetyl group.
