Generation of Complex Azabicycles and Carbobicycles from Two Simple Compounds in a Single Operation through a Metal-Free Six-Step Domino Reaction

Beitrag in einer Fachzeitschrift
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Details zur Publikation

Autor(en): Bock C, Parameshwarappa G, Bönisch S, Neiß C, Bauer W, Hampel F, Görling A, Tsogoeva S
Zeitschrift: Chemistry - A European Journal
Jahr der Veröffentlichung: 2016
Band: 22
Heftnummer: 15
Seitenbereich: 5189-5197
ISSN: 0947-6539


Abstract


Aza- and carbobicyclic compounds possess favorable pharmaceutical properties, but they are difficult to access. Herein, we demonstrate an unprecedented organocatalytic two component six-step chemodivergent domino reaction, which provides a straightforward, sustainable and atom economical route to difficult-to-access complex bicyclic architectures: azabicycles and carbobicycles, whose ratios can be controlled by the applied electrophiles and catalysts. Detailed NMR and X-ray studies on the structures and relative stereochemistry of selected compounds are presented. Mechanistic investigations of the chemoselective branching step have been carried out with DFT methods in conjunction with semiempirical van der Waals interactions. This new domino reaction opens up a new vista of generating, in a single operation, new bioactive compounds with strong antiviral properties (EC50 up to 0.071 μM for human cytomegalovirus (HCMV)) outperforming clinically used ganciclovir (EC50 2.6 μM).



FAU-Autoren / FAU-Herausgeber

Bock, Christina
Professur für Organische Chemie
Bönisch, Simon
Lehrstuhl für Theoretische Chemie
Görling, Andreas Prof. Dr.
Lehrstuhl für Theoretische Chemie
Hampel, Frank Dr.
Lehrstuhl für Organische Chemie I
Neiß, Christian Dr.
Lehrstuhl für Theoretische Chemie
Tsogoeva, Svetlana Prof. Dr.
Professur für Organische Chemie


Zitierweisen

APA:
Bock, C., Parameshwarappa, G., Bönisch, S., Neiß, C., Bauer, W., Hampel, F.,... Tsogoeva, S. (2016). Generation of Complex Azabicycles and Carbobicycles from Two Simple Compounds in a Single Operation through a Metal-Free Six-Step Domino Reaction. Chemistry - A European Journal, 22(15), 5189-5197. https://dx.doi.org/10.1002/chem.201504798

MLA:
Bock, Christina, et al. "Generation of Complex Azabicycles and Carbobicycles from Two Simple Compounds in a Single Operation through a Metal-Free Six-Step Domino Reaction." Chemistry - A European Journal 22.15 (2016): 5189-5197.

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Zuletzt aktualisiert 2018-16-11 um 20:50