Synthesis p. 797 - 802 (1993)
Update date:2022-09-26
Topics:
Merz
Rauschel
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.
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(2014)Doi:10.1016/j.tet.2016.09.059
(2016)Doi:10.1002/anie.201404355
(2014)Doi:10.1016/S0040-4039(00)79306-3
(1993)