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  • Title: Synthesis of diazatricyclic core of Madangamines from cis-perhydroisoquinolines.
    Author: Quirante J, Paloma L, Diaba F, Vila X, Bonjoch J.
    Journal: J Org Chem; 2008 Jan 18; 73(2):768-71. PubMed ID: 18095709.
    Abstract:
    Synthesis of the tricyclic core of madangamine alkaloids has been achieved in a 10-step sequence starting from a 4-(aminomethyl)anisole derivative. A Birch reduction and acylation with cyanoacetic acid followed by an intramolecular Michael process renders a polyfunctionalized cis-perhydroisoquinoline. A diastereoselective allylation and reduction of amide, nitrile, and ketone groups leads to a bicyclic alcohol, which undergoes aminocyclization through the nosyl derivative to the diazatricyclic ring.
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