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ID 113634
Title Alternative
Direct Synthesis of Polycyclic Tropinones via Condensation-(4+3) Cycloaddition Cascade Reaction
Author
Okamoto, Tsubasa Tokushima University
Shibata, Miki Tokushima University
Yoshida, Masahiro Tokushima bunri University KAKEN Search Researchers
Keywords
synthetic method
cycloaddition
tropane alkaloid
pyrrole
oxyallyl cation
Content Type
Journal Article
Description
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.
Journal Title
Chemistry- A European Journal
ISSN
15213765
09476539
NCID
AA11076269
Publisher
Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Volume
24
Issue
38
Start Page
9508
End Page
9513
Published Date
2018-04-27
Rights
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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language
eng
TextVersion
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departments
Pharmaceutical Sciences