[reaction: see text] The trimeric quinone framework of conocurvone is crucial for its potent anti-HIV activity. A new synthesis of trimeric quinones based on stepwise substitution of the halogens in 2,3-dihaloquinones by hydroxyquinone anions is described. Chlorinated biquinones are key intermediates that undergo regiospecific substitution reactions to yield trimeric quinone monomethyl ethers.

2002quinones quinones (naphthalene compounds) Q 0910 -089Regiocontrolled Synthesis of the Trimeric Quinone Framework of Conocurvone.-A simple and efficient method for the formation of quinone-quinone bonds is developed by using hydroxyquinone anions as nucleophiles in quinone substitution reactions. The investigation is presented in connection with studies on the synthesis of the HIV inhibitor conocurvone. -(EMADI, ASHKAN; HARWOOD, JOHN S.; KOHANIM, SAHAR; STAGLIANO, KENNETH W.;