- Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps
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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.
- Jagtap, Pratap R.,Císa?ová, Ivana,Jahn, Ullrich
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supporting information
p. 750 - 755
(2018/02/09)
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- New Reagent Systems Containing CrO3 Provide Precursors for Syntheses of Neo-lignans
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Oxidations of 1-aryl-1-propenes with new reagent systems, CrO3-HBF4-MeCN and CrO3-HClO4-MeCN, gave the 4-aryltetralones 1a and 1c, and the tetrahydrofuran 4, which are precursor molecules for aryltetrahydronaphthalene and tetrahydrofuran neo-lignans.Keywords - reagent system: chromium trioxide, neo-lignan; aryltetrahydronaphthalene; tetrahydrofuran
- Takeya, Tetsuya,Matsumoto, Hiroshi,Kotani, Eiichi,Tobinaga, Seisho
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p. 4364 - 4367
(2007/10/02)
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- New Reagent System containing CrO3 and Syntheses of Neo-lignans
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Oxidations of 1-arylprop-1-enes by the new reagent systems, CrO3-HBF4-MeCN or CrO3-HClO4-MeCN gave the 4-aryltetralones (1a) and (1c), and the tetrahydrofuran (3) which are precursor molecules for aryltetrahydronaphthalene and tetrahydrofuran neo-lignans.
- Takeya, Tetsuya,Kotani, Eiichi,Tobinaga, Seisho
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