MERZ, A and RAUSCHEL, M (1993) SYNTHESIS OF CROWN-ETHERS RELATED TO UBIQUINONES. SYNTHESIS-STUTTGART (8). pp. 797-802. ISSN 0039-7881,
Full text not available from this repository.Abstract
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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | LINEAR POLYPRENOIDS; QUINONES; |
| Depositing User: | Dr. Gernot Deinzer |
| Last Modified: | 19 Oct 2022 08:42 |
| URI: | https://pred.uni-regensburg.de/id/eprint/53873 |
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