Stereoselective Synthesis of Novel (±)-trans-Dihydronarciclasine Analogues: Preparation of a Pivotal Intermediate Containing Two Methoxy Substituents

Authors

  • Balázs Lévai
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • Gábor Varró
    Affiliation
    Gedeon Richter Plc., Gyömrői út 19-21., H-1103 Budapest, Hungary
  • András Simon
    Affiliation
    Department of Inorganic and Analytical Chemistry, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • László Hegedűs
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • István Kádas
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
https://doi.org/10.3311/PPch.20438

Abstract

An efficient stereoselective synthesis of a pivotal intermediate, a cyclic allyl alcohol derivative containing two methoxy groups [(±)-22], using for the preparation of (±)-trans-dihydronarciclasine analogues was elaborated starting from easily available and inexpensive methyl gallate. This new synthetic route consists of 17 reaction steps, and provides an opportunity to obtain the wanted alkaloid derivative containing an additional methoxy group at position 11, in the ring A of the phenanthridone scaffold.

Keywords:

alkaloids, phenanthridone scaffold, stereoselective synthesis

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Published Online

2023-02-01

How to Cite

Lévai, B., Varró, G., Simon, A., Hegedűs, L., Kádas, I. “Stereoselective Synthesis of Novel (±)-trans-Dihydronarciclasine Analogues: Preparation of a Pivotal Intermediate Containing Two Methoxy Substituents”, Periodica Polytechnica Chemical Engineering, 67(1), pp. 31–40, 2023. https://doi.org/10.3311/PPch.20438

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