Ether cleavage of 7-oxabicyclo[2,2,1]heptane derivatives

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Abstract
In connection with the total synthesis of natural products containing a 2-hydroxycyclohexane-carboxylic acid or -1,5-carbolactone system, ether cleavage of 1-methyl-7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acids and their methyl esters was achieved. The products included 6-acetoxy-3-methylcyclohex-3-ene-1,2-dicarboxylic anhydride, the corresponding dicarboxylic acids and cis-dimethyl ester, 1-methylcyclohexane-2,4:3,1-biscarbolactone, 6-acetoxy-2-carboxy-3-methylcyclohexane-1,3-carbolactone, and dimethyl 3,6-diacetoxy-3-methylcyclohexane-1,2-dicarboxylate.

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