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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

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.

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 Creators:
Feilcke, Ruth1, Author
Goddard, Richard2, Author              
Imming, Peter1, Author
Seidel, Rüdiger W.1, Author
Affiliations:
1Institut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Straße 4, 06120 Halle (Saale), Germany, ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: Oxoassoanine; N-Acylindoline; Phenanthridone; Palladium; Crystal structure
 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.

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Language(s): eng - English
 Dates: 2018-10-092018-07-192018-10-102018-10-152019-02-15
 Publication Status: Published in print
 Pages: 11
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/j.molstruc.2018.10.031
 Degree: -

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Title: Journal of Molecular Structure
Source Genre: Journal
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Publ. Info: Amsterdam : Elsevier
Pages: - Volume / Issue: 1178 (2) Sequence Number: - Start / End Page: 341 - 351 Identifier: ISSN: 0022-2860
CoNE: https://pure.mpg.de/cone/journals/resource/954925415947