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  • Title: Concise asymmetric syntheses of novel phenanthroquinolizidines.
    Author: Anton-Torrecillas C, Loza MI, Brea J, Gonzalez-Gomez JC.
    Journal: Org Biomol Chem; 2016 Feb 21; 14(7):2264-71. PubMed ID: 26790584.
    Abstract:
    The first preparation of enantioenriched phenanthroquinolizidines with a quaternary center at C14a was accomplished in seven steps from readily available starting materials. Key steps were an efficient dynamic kinetic allylation of a diastereomeric mixture of chiral tert-butylsulfinyl ketimines and the construction of a piperidine E ring by rhodium catalyzed hydroformylation. The Stevens rearrangement of the corresponding N-benzyl derivatives took place smoothly, allowing the installation of a benzyl moiety at C9 in a trans relationship with the methyl group. The cytoxicity of the prepared phenanthroquinolizidines was evaluated against different human cancer cell lines.
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