
%0 Journal Article
%A Carvalho, CF 
%A Russo, AV 
%A Sargent, MV 
%T Boron, Trichloride as a Selective Demethylating Agent for Hindered Ethers: a Synthesis of the Phytoalexins &#945;- and &#914;-Pyrufuran, a Synthesis of Tri-<i>O</i>-methylleprolomin and its Demethylation
%J Australian Journal of Chemistry
%D 1985/05/01
%V 38
%N 5
%P 777-792
%K 
%R https://doi.org/10.1071/CH9850777
%U https://www.publish.csiro.au/paper/CH9850777 
%X Boron trichloride has been found to be an efficient reagent for the selective cleavage of sterically hindered methoxy groups in methoxyarenes . The scope and utility of this reaction are explored with examples drawn from derivatives of benzene, naphthalene, 9,10- dihydrophenanthrene and dibenzofuran. The method is applied to the synthesis of the phytoalexins &#945;-(56) and &#946;- pyrufuran (58) (1,3,4- trimethoxydibenzofuran-2-ol and 1,2,4-trimethoxydibenzofuran-3-ol). A synthesis of tri-O- methylleprolomin (61), a derivative of the unusual lichen metabolite leprolomin (60), is described and its demethylation with boron trichloride is studied. 
