Concise asymmetric syntheses of novel phenanthroquinolizidines

Organic & Biomolecular Chemistry
Cintia Anton-TorrecillasJose C Gonzalez-Gomez

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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Citations

Nov 27, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Francisco Foubelo, Miguel Yus
Jun 8, 2021·Beilstein Journal of Organic Chemistry·Joseane A MendesCamilla D Buarque

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