TY - JOUR
T1 - An enantioselective total synthesis of the stilbenolignan (-)-aiphanol and the determination of its absolute stereochemistry
AU - Banwell, Martin G.
AU - Chand, Satish
AU - Savage, G. Paul
PY - 2005/5/2
Y1 - 2005/5/2
N2 - The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-β to give triol (1R,2R)-1-(3′,5′-dimethoxy-4′-methoxymethoxyphenyl) -2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2′ and C-3′.
AB - The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-β to give triol (1R,2R)-1-(3′,5′-dimethoxy-4′-methoxymethoxyphenyl) -2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2′ and C-3′.
UR - http://www.scopus.com/inward/record.url?scp=17844397970&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2005.02.035
DO - 10.1016/j.tetasy.2005.02.035
M3 - Article
SN - 0957-4166
VL - 16
SP - 1645
EP - 1654
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 9
ER -