Expedient two-step synthesis of phenolic cyclitols from benzene.
The benzeneselenol-catalyzed, tributyltin hydride-mediated addition of phenolic iodides to benzene gives the 3-(hydroxyaryl)-1,4-cyclohexadienes, predominantly. Under conditions of controlled osmoylation, these are converted to the racemic 1,2-syn-2,3-anti-3-(hydroxyaryl)-4-cyclohexene-1,2-diols, whereas exhaustive osmoylation gives the 3-(hydroxyaryl)-3,5-dideoxymucoinositols, whose stereochemistry is established by X-ray crystallography.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Grant
Daniel
D
Wink
Donald J
DJ
D001554:Benzene / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007294:Inositol / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis*; D013237:Stereoisomerism
D010636:Phenols; D007294:Inositol; D001554:Benzene