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Organic letters

Solvent-controlled leaving-group selectivity in aromatic nucleophilic substitution.


PMID 18841994

Abstract

A solvent-controlled inversion of leaving group ability allows selective access to either of two internal substitution products in S(N)Ar reactions of substrates with competing leaving groups. Application of this principle in a selective synthesis of the highly functionalized xanthone core of the antibiotic FD-594 is presented.

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