A short asymmetric synthesis of (+)-lyoniresinol dimethyl ether.
A short, efficient synthesis of the lignan (+)-lyoniresinol dimethyl ether is described. The synthesis is achieved by asymmetric photocyclization of an achiral dibenzylidenesuccinate to a chiral aryldihydronaphthalene. (-)-Ephedrine is used as a chiral auxiliary to bias the atropisomeric equilibrium in the dibenzylidenesuccinate prior to the photochemical reaction. The synthesis of the title compound was accomplished in five steps, and the final product was recrystallized to constant melting point and rotation.
Assoumatine
Tokouré
T
Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, Canada R3T 2N2.
Datta
Probal K
PK
Hooper
Timothy S
TS
Yvon
Brigitte L
BL
Charlton
James L
JL