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Issue 7, 2016
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Concise asymmetric syntheses of novel phenanthroquinolizidines

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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.

Graphical abstract: Concise asymmetric syntheses of novel phenanthroquinolizidines

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The article was received on 21 Dec 2015, accepted on 13 Jan 2016 and first published on 21 Jan 2016

Article type: Paper
DOI: 10.1039/C5OB02624E
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Org. Biomol. Chem., 2016,14, 2264-2271

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    Concise asymmetric syntheses of novel phenanthroquinolizidines

    C. Anton-Torrecillas, M. I. Loza, J. Brea and J. C. Gonzalez-Gomez, Org. Biomol. Chem., 2016, 14, 2264
    DOI: 10.1039/C5OB02624E

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