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Synthesis 1993; 1993(8): 797-802
DOI: 10.1055/s-1993-25945
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Synthesis of Crown Ethers Related to Ubiquinones

Andreas Merz* , Manfred Rauschel
  • *Institut für Organische Chemie, Universität Regensburg, Universitätsstraße 31, D-8400 Regensburg, Germany
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Publication History

Publication Date:
27 September 2002 (online)

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Crown ethers in which the two methoxy groups of ubiquinone-0 (2,3-dimethoxy-5-methyl-1, 4-benzoquinone) are replaced by oligoethylene glycol bridges have been obtained in five straightforward steps in 35-40% overall yield from 5-methylpyrogallol. A Fremy salt oxidation of a phenolic precursor is used in the final step. The further elaboration of crown ether analogues of ubiquinone-2 was achieved by enol geranylation of cyclopentadiene adducts of the former quinones and subsequent retro-Diels-Alder reaction. The Claisen rearrangement of 2, 2-dimethoxy-5-methylphenyl allyl ethers and related crown ethers affords ortho- and para-allyl-substituted phenols (3: 1) that are oxidized to give bisnorubiquinone derivatives and their ortho- quinone isomers. All new compounds are characterized by high resolution NMR and mass spectrometry.