Stereocontrolled Access to Benzo-Annelated all-cis- and cis,cis,cis,trans-[5.5.5.6]Fenestranones and all-cis-[5.5.5.5]Fenestranes

Bredenkötter B, Linke J, Kuck D (2017)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (30): 4414-4428.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor/in
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Abstract / Bemerkung
The synthesis of three multiply substituted fenestrindanes (all-cis-tetrabenzo[5.5.5.5]fenestranes) is described in detail. Depending on the stereochemical course of the twofold Michael addition of a 1,3-indanedione to a dibenzylideneacetone in the very first step, the corresponding all-cis-tribenzo[5.5.5.6]fenestranones or the strained cis,cis,cis,trans isomers are obtained. In the latter case, stereochemical adjustment to the all-cis configuration can be achieved by base-induced epimerization. Conversion of the all-cis-[5.5.5.6]fenestranones in five subsequent steps affords the target fenestrindanes bearing either methyl groups at four of the inner (bay) positions or methoxy groups at four or six of the outer (peripheral) positions of the molecular framework.
Stichworte
Polycyclic compounds; Fenestranes; Spiro compounds; Michael addition; Ketones; Epimerization
Erscheinungsjahr
2017
Zeitschriftentitel
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Ausgabe
30
Seite(n)
4414-4428
ISSN
1434-193X
eISSN
1099-0690
Page URI
https://pub.uni-bielefeld.de/record/2913978

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Bredenkötter B, Linke J, Kuck D. Stereocontrolled Access to Benzo-Annelated all-cis- and cis,cis,cis,trans-[5.5.5.6]Fenestranones and all-cis-[5.5.5.5]Fenestranes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2017;(30):4414-4428.
Bredenkötter, B., Linke, J., & Kuck, D. (2017). Stereocontrolled Access to Benzo-Annelated all-cis- and cis,cis,cis,trans-[5.5.5.6]Fenestranones and all-cis-[5.5.5.5]Fenestranes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(30), 4414-4428. doi:10.1002/ejoc.201700752
Bredenkötter, B., Linke, J., and Kuck, D. (2017). Stereocontrolled Access to Benzo-Annelated all-cis- and cis,cis,cis,trans-[5.5.5.6]Fenestranones and all-cis-[5.5.5.5]Fenestranes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 4414-4428.
Bredenkötter, B., Linke, J., & Kuck, D., 2017. Stereocontrolled Access to Benzo-Annelated all-cis- and cis,cis,cis,trans-[5.5.5.6]Fenestranones and all-cis-[5.5.5.5]Fenestranes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (30), p 4414-4428.
B. Bredenkötter, J. Linke, and D. Kuck, “Stereocontrolled Access to Benzo-Annelated all-cis- and cis,cis,cis,trans-[5.5.5.6]Fenestranones and all-cis-[5.5.5.5]Fenestranes”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, pp. 4414-4428.
Bredenkötter, B., Linke, J., Kuck, D.: Stereocontrolled Access to Benzo-Annelated all-cis- and cis,cis,cis,trans-[5.5.5.6]Fenestranones and all-cis-[5.5.5.5]Fenestranes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 4414-4428 (2017).
Bredenkötter, Björn, Linke, Jens, and Kuck, Dietmar. “Stereocontrolled Access to Benzo-Annelated all-cis- and cis,cis,cis,trans-[5.5.5.6]Fenestranones and all-cis-[5.5.5.5]Fenestranes”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 30 (2017): 4414-4428.