The First Enantioselective Total Synthesis of (−)-trans-Dihydronarciclasine

Varró, Gábor and Hegedűs, László and Simon, András and Balogh, Attila and Grün, Alajos and Leveles, Ibolya and Vértessy, G. Beáta and Kádas, István (2017) The First Enantioselective Total Synthesis of (−)-trans-Dihydronarciclasine. JOURNAL OF NATURAL PRODUCTS, 80 (6). pp. 1909-1917. ISSN 0163-3864

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Abstract

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.

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