Synthesis of 5,8-dimethoxy-3-hydroxy-4-quinolone, a reported inhibitor of HIV RT, and evidence the original proposed structure was incorrect

An unambiguous total synthesis of the title compound, a semi-synthetic deri vative reported to be a non-nucleoside reverse transcriptase inhibitor, was conducted in four steps from 2,5-dimethoxyaniline. The synthetic material differed from that reported in the literature, both in its physical propert ies and H-1 NMR spectrum. Biological evaluation indicated that synthetic 2 was inactive against HIV-1 RT, suggesting that the previous structural assi gnment of the semi-synthetic derivative was incorrect. (C) 1999 Elsevier Sc ience Ltd. Air rights reserved.