AN EFFICIENT SYNTHESIS OF OPTICALLY PURE ANTHRACYCLINONE INTERMEDIATES BY THE NOVEL USE OF MICROBIAL REDUCTION

Article abstract of DOI:10.1016/S0040-4039(00)88665-7

Reduction of the racemic α-hydroxy ketones((+/-)-3a,b) with fermenting baker's yeast followed by fractional recrystallization and oxidation was found to readily afford optically pure anthracyclinone intermediates((R)(-)-3a,b) and their partially optically active antipodes((S)(+)-3a,b).The useless enantiomers((S)(+)-3a,b) and diastereomeric vicinal-diols((+)-5a,b) could be recycled to (+/-)-3a,b and the achiral ketones(6a,b) by racemization and oxidative cleavage, respectively.