A simple and efficient highly enantioselective synthesis of alpha-ionone and alpha-damascone

An efficient highly enantioselective (ee > or =99%) synthesis of alpha-ionone and alpha-damascone is described. Both enantiomers of title compounds were synthesized through two straightforward pathways diverging from enantiopure (R)- or (S)-alpha-cyclogeraniol. These versatile building blocks were obtained by regioselective ZrCl(4)-promoted biomimetic cyclization of (6S)- or (6R)-(Z)-6,7-epoxygeraniol, respectively, followed by deoxygenation of the so formed secondary alcohol. The chiral information was encoded by a highly regioselecive Sharpless asymmetric dihydroxylation of inexpensive geranyl acetate.