A structural study of seven N-acylindolines and their Pd(II)-mediated 
intramolecular oxidative coupling reactions for the synthesis of 
pyrrolophenanthridone alkaloids

Feilcke, Ruth; Goddard, Richard; Imming, Peter; Seidel, Rüdiger W.

doi:10.1016/j.molstruc.2018.10.031

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A structural study of seven N-acylindolines and their Pd(II)-mediated intramolecular oxidative coupling reactions for the synthesis of pyrrolophenanthridone alkaloids

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Goddard, Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Feilcke, R., Goddard, R., Imming, P., & Seidel, R. W. (2019). A structural study of seven N-acylindolines and their Pd(II)-mediated intramolecular oxidative coupling reactions for the synthesis of pyrrolophenanthridone alkaloids. Journal of Molecular Structure, 1178(2), 341-351. doi:10.1016/j.molstruc.2018.10.031.

Cite as: https://hdl.handle.net/21.11116/0000-0002-C5FE-2

Abstract

Direct synthesis of the pyrrolophenanthridone scaffold was explored using an intramolecular Pd(II)-mediated coupling reaction of different N-acylindolines via C-H activation. Amaryllidaceae alkaloids of the lycorine type belong to this type. Depending on the substitution pattern of the starting materials, the pathway yielded different product patterns and yields. Introduction of electron-withdrawing substituents into the 6-position of the indoline moiety did not improve coupling. Seven N-acylindoline precursors were structurally characterized by X-ray crystallography and NMR spectroscopy. The crystal structure of the lycorine type alkaloid oxoassoanine is reported for the first time.