Direct Synthesis of Polycyclic Tropinones via Condensation-(4+3) Cycloaddition Cascade Reaction
Okamoto, Tsubasa Tokushima University
Shibata, Miki Tokushima University
Karanjit, Sangita Tokushima University Tokushima University Educator and Researcher Directory
Nakayama, Atsushi Tokushima University Tokushima University Educator and Researcher Directory KAKEN Search Researchers
Namba, Kosuke Tokushima University Tokushima University Educator and Researcher Directory KAKEN Search Researchers
A concise method of constructing polycyclic tropinone frameworks was developed. The single-step synthesis of polycyclic tropinone consists of an intramolecular (4+3) cycloaddition reaction of N-nosyl-pyrrole with oxyallyl cation that was generated in situ by an intermolecular condensation reaction of the nucleophilic functional groups on a tethered pyrrole with the aldehyde of 2-(silyloxy)-acrolein. This cascade reaction afforded various polycyclic tropinones including tri-, tetra-, and pentacyclic systems in high yields as single diastereomers.
Chemistry- A European Journal
Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
This is the peer reviewed version of the following article: T. Okamoto, M. Shibata, S. Karanjit, A. Nakayama, M. Yoshida, K. Namba, Chem. Eur. J. 2018, 24, 9508, which has been published in final form at https://doi.org/10.1002/chem.201802011. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
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