Highly stereoselective and stereospecific syntheses of a variety of quercitols from D-(-)-quinic acid

The highly stereoselective synthesis of (-)-epi-, (-)-allo- and neo-quercitols as well as stereospecific synthesis of (-)-talo-and (+)-gala-quercitols have been achieved. The general strategy is employing dihydroxylation of the isolated double bond of various kinds of protected chiral (1,4,5)-cyclohex-2-ene-triols, which are derived from D-(-)-quinic acid. The choosing of protecting groups from either BBA (butane 2,3-bisacetal) or acetyl groups will result in the various degrees of stereoselectivity of dihydroxylation. On the other hand, the cyclohexylidene acetal moiety is attributed to the stereospecificity during dihydroxylation to afford the request molecules. (C) 2004 Elsevier Ltd. All rights reserved.