461641-26-9Relevant academic research and scientific papers
Total synthesis of (-)-20-epiuleine via stereocontrolled one-pot asymmetric azaelectrocyclization followed by novel 1,4-addition reaction
Sakaguchi, Taku,Kobayashi, Shohei,Katsumura, Shigeo
scheme or table, p. 257 - 264 (2011/02/24)
The first asymmetric total synthesis of an indole alkaloid, (-)-20-epiuleine, containing the 2,3,4-trisubstituted piperidine core, was achieved using a stereocontrolled one-pot asymmetric 6π-azaelectrocyclization followed by a stereoselective 1,4-addition
Development of highly stereoselective asymmetric 6π- azaelectrocyclization of conformationally flexible linear 1-azatrienes. From determination of multifunctional chiral amines, 7-alkyl cis-1-amino-2-indanols, to application as a new synthetic strategy: Formal synthesis of 20-epiuleine
Tanaka, Katsunori,Kobayashi, Toyoharu,Mori, Hajime,Katsumura, Shigeo
, p. 5906 - 5925 (2007/10/03)
The highly stereoselective asymmetric 6π-azaelectrocyclization was achieved as a general synthetic method based on the reaction between the (E)-3-carbonyl-2,4,6-trienal compounds and the (-)-7-alkyl-cis-l-amino-2-indanol derivatives which are effective chiral amines. The 7-alkyl-substituted 2-indanol moiety of the cyclized products was efficiently removed by the novel manganese dioxide oxidation under remarkably mild conditions, and the method was successfully applied to the formal synthesis of optically active 20-epiuleine.
Highly stereoselective asymmetric 6π-azaelectrocyclization utilizing the novel 7-alkyl substituted cis-1-amino-2-indanols: Formal synthesis of 20-epiuleine
Tanaka, Katsunori,Katsumura, Shigeo
, p. 9660 - 9661 (2007/10/03)
Highly stereoselective asymmetric 6π-azaelectrocyclization was achieved with generality, based on the reaction between the (E)-3-carbonyl-2,4,6-trienal compounds and the (-)-7-alkyl-cis-1-amino-2-indanol derivatives as the effective novel chiral amines. F
