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

Organic & Biomolecular Chemistry Pub Date: 2009-10-15 DOI: 10.1039/B916969E

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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