815581-77-2Relevant articles and documents
A simple and efficient highly enantioselective synthesis of α-ionone and α-damascone
Bovolenta, Marcella,Castronovo, Francesca,Vadala, Alessandro,Zanoni, Giuseppe,Vidari, Giovanni
, p. 8959 - 8962 (2004)
An efficient highly enantioselective (ee ≥99%) synthesis of α-ionone and α-damascone is described. Both enantiomers of title compounds were synthesized through two straightforward pathways diverging from enantiopure (R)- or (S)-α-cyclogeraniol. These versatile building blocks were obtained by regioselective ZrCl4-promoted biomimetic cyclization of (6S)- or (6E)-(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.