1263486-03-8Relevant articles and documents
The First Enantioselective Total Synthesis of (-)-Trans-Dihydronarciclasine
Varró, Gábor,Hegedus, László,Simon, András,Balogh, Attila,Grün, Alajos,Leveles, Ibolya,Vértessy, Beáta G.,Kádas, István
, p. 1909 - 1917 (2017)
A feasible and enantioselective total synthesis of (-)-Trans-dihydronarciclasine [(-)-1], a highly biologically active alkaloid, was devised starting from vanillin (8). The key step of this new synthesis was an asymmetric, organocatalytic Michael addition, in which an optically active nitropentanone [(-)-13] was obtained from a butenone derivative (12). Excellent enantioselectivity (>99% ee) was achieved using the (8S,9S)-9-Amino(9-deoxy)epiquinine (16) organocatalyst. The target molecule can be prepared in 13 steps from compound (-)-13. The total synthesis has provided a facile and first access to the ent-form of naturally occurring (+)-Trans-dihydronarciclasine, a highly potent cytostatic alkaloid.