SYNTHESIS OF CROWN-ETHERS RELATED TO UBIQUINONES

被引:0
作者
MERZ, A
RAUSCHEL, M
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SYNTHESIS-STUTTGART | 1993年 / 08期
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O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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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页码:797 / 802
页数:6
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