A DOUBLE DIELS-ALDER REACTION OF A C2-SYMMETRIC BIS-DIENOPHILE: A NEW ENANTIOSELECTIVE APPROACH TO NATURAL LOGANIN

Article abstract of DOI:10.1016/S0040-4039(00)96440-2

Reaction of a chiral C₂-symmetric bis-dienophile 1 and cyclopentadiene gave a mixture (3:2) of adducts 2 and 3 of which the major one was converted into a key intermediate 12 of loganin.The formation of the adducts is presumed via the anti-Felkin-Anh type active conformers, 14 and 15, respectively.