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.
Bovolenta
Marcella
M
Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, 27100 Pavia, Italy.
Castronovo
Francesca
F
Vadalà
Alessandro
A
Zanoni
Giuseppe
G
Vidari
Giovanni
G
D008968:Molecular Conformation; D045792:Norisoprenoids / Q000138:chemical synthesis*; D013237:Stereoisomerism
D045792:Norisoprenoids; C011879:alpha-ionone