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Issue 15, 2000
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Diastereoselective oxygen to carbon rearrangements of anomerically linked enol ethers and the total synthesis of (+)-(S,S<img border='0' src='http://www.rsc.org/images/entities/h2_char_200a.gif' alt=' '/>)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, a component of civet

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Abstract

A range of enol ethers, linked via their oxygen atom to the anomeric centre of a pyran ring system, was shown to undergo oxygen to carbon rearrangement upon treatment with a Lewis acid to give the corresponding 2-carbon substituted products. At low temperature, trimethylsilyl trifluoromethanesulfonate catalysed rearrangements of anomerically linked 6-substituted tetrahydropyranyl enol ethers gave selectively the trans-pyranyl ketones, whereas at higher temperatures selective formation of the cis-pyranyl ketones was observed. In a simple application of the methodology the cis-selective rearrangement was used as the key step in a concise total synthesis of a constituent of civet.

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Publication details

The article was received on 15 Feb 2000, accepted on 27 Mar 2000 and first published on 10 May 2000


Article type: Paper
DOI: 10.1039/B001243M
Citation: J. Chem. Soc., Perkin Trans. 1, 2000, 2385-2394
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    Diastereoselective oxygen to carbon rearrangements of anomerically linked enol ethers and the total synthesis of (+)-(S,S<img border='0' src='http://www.rsc.org/images/entities/h2_char_200a.gif' alt=' '/>)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, a component of civet

    D. J. Dixon, S. V. Ley and E. W. Tate, J. Chem. Soc., Perkin Trans. 1, 2000, 2385
    DOI: 10.1039/B001243M

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