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Issue 5, 2018
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Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

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Abstract

A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.

Graphical abstract: Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

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Publication details

The article was received on 20 Nov 2017, accepted on 08 Dec 2017 and first published on 12 Dec 2017


Article type: Paper
DOI: 10.1039/C7OB02848B
Citation: Org. Biomol. Chem., 2018,16, 750-755
  • Open access: Creative Commons BY-NC license
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    Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

    P. R. Jagtap, I. Císařová and U. Jahn, Org. Biomol. Chem., 2018, 16, 750
    DOI: 10.1039/C7OB02848B

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