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J Nat Prod. 2017 Jun 23;80(6):1909-1917. doi: 10.1021/acs.jnatprod.7b00208. Epub 2017 Jun 5.

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

Author information

1
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics , Budafoki út 8, H-1111 Budapest, Hungary.
2
MTA-BME Organic Chemical Technology Research Group, Hungarian Academy of Sciences, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics , Budafoki út 8, H-1111 Budapest, Hungary.
3
Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics , Szt. Gellért tér 4, H-1111 Budapest, Hungary.
4
Institute of Enzymology, Research Centre for Natural Sciences, Hungarian Academy of Sciences , Magyar tudósok körútja 2, H-1117 Budapest, Hungary.
5
Department of Applied Biotechnology and Food Science, Budapest University of Technology and Economics , Szt. Gellért tér 4, H-1111 Budapest, Hungary.

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.

PMID:
28581297
DOI:
10.1021/acs.jnatprod.7b00208
[Indexed for MEDLINE]

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