Regiocontrolled synthesis of the trimeric quinone framework of conocurvone.
[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.
Emadi
Ashkan
A
Department of Biological, Chemical, and Physical Sciences, Illinois Institute of Technology, Chicago, Illinois 60616, USA.
Harwood
John S
JS
Kohanim
Sahar
S
Stagliano
Kenneth W
KW
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D005374:Filtration; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D007202:Indicators and Reagents; D009285:Naphthoquinones; D011809:Quinones; C091977:conocurvone