A stereoselective synthesis of a chiral anthracyclinone AB-synthon from a carbohydrate precursor

Reaction of tetralinol 5 with phenylboronic acid removed the isopropylidene group with concomitant formation of phenylboronate 12. Oxidation of the latter with PCC gave keto-ester 13, a key intermediate in the synthesis of enantiopure anthracyclinones. Attempts at cleavage of the isopropylidene group in 5 by the usual procedures led first to substitution and epimerization at the benzylic position, then removal of the acetonide followed by formation of the cyclic ether 11a as the final product. (C) 2005 Elsevier Ltd. All rights reserved.