A New Approach to the Total Synthesıs of (±)-Nordasycarpıdone by Rıng-closure wıth Tetrachloro-1,4-benzoquınone

Nesimi Uludag

Abstract


A new synthetic route for the  (±)-nordasycarpidone was achieved in five steps with an overall yield of  41%. This route involves  ring closure and formation of 5 which has a  methanoazocino[4,3-b]indole skeleton in the key step. The reaction also involved a cyclization reaction of  tetrahydrocarbazole with a monoalkyl nitrile side chain at the C-2 position, and this reaction was mediated by tetrachloro-1,4-benzoquinone (TCB). The central step in the synthesis was  the closure of the D-ring of the intra-molecular structure and the addition of amine, which resulted in an aza-tetracyclic substructure that contained the ABCD-ring of the strychnos alkaloid family.


Keywords


dasycarpidone; uleine; nordasycarpidone; 1,5-methanoazacino[4,3-b]indole

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References


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DOI: http://dx.doi.org/10.20450/mjcce.2020.1736

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