Recent methods for demethylating aryl methyl ethers have been briefly reviewed, especially
methods involving the use of nucleophilic reagents. Sodium thioethoxide
dissolved in N,N-dimethylformamide
has been developed as a powerful new reagent for demethylating
aryl methyl ethers cleanly and rapidly in high yield. The reaction conditions
can be controlled so that aromatic bromo substituents or isolated olefinic bonds are unaffected. Of special interest has
been the selective monodemethylation of the methyl
ethers of di- and tri-hydric
phenols, exemplified by the isolation in high yield of orcinol
monomethyl ether, p-methoxyphenol, guaiacol, and phloroglucinol dimethyl ether
from the respective fully O-methylated
compounds. An exception was pyrogallol trimethyl ether which afforded
pyrogallol 1-monomethyl ether in high yield.
Culture filtrates of Nectria radicicola Gerlach & Nilsson yielded
two products: a peptide fraction, "radicicolin",
and a phenolic substance, radicicol (monorden), C18H17ClO6.
Chemical and spectroscopic studies showed that radicicol
was a macrolide with structure (Ia).
Brefeldin A was isolated from filtrates of other
strains of the organism.
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