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Issue 24, 2009
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Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products

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Abstract

An efficient selective demethylation and debenzylation method for aryl methyl/benzyl ethers using magnesium iodide under solvent-free conditions has been developed and applied to the synthesis of natural flavone and biphenyl glycosides. A variety of functional groups including glycoside were tolerated under the reaction conditions. Experimental results indicated that the removal of an O-benzyl group was easier than that of an O-methyl group, regardless of wherever they were meta or para to the carbonyl. Thus selective debenzylation can be achieved for substrates bearing both benzyloxy and methoxy groups.

Graphical abstract: Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products

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Publication details

The article was received on 17 Aug 2009, accepted on 16 Sep 2009 and first published on 15 Oct 2009


Article type: Paper
DOI: 10.1039/B916969E
Citation: Org. Biomol. Chem., 2009,7, 5084-5090
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    Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products

    K. Bao, A. Fan, Y. Dai, L. Zhang, W. Zhang, M. Cheng and X. Yao, Org. Biomol. Chem., 2009, 7, 5084
    DOI: 10.1039/B916969E

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