Enantioselective synthesis of (R)-(-)-laudanosine and (R)-(-)-glaucine from L-ascorbic acid

Article abstract of DOI:10.1016/0957-4166(96)00349-7

L-Ascorbic acid 1 was converted into L-gulonolactone 2 by catalytic hydrogenation. Treatment of 2 with 3,4-dimethoxyphenylethyl amine 3 afforded amide 4, which in several steps was transformed into the title alkaloids in good enantiomeric excesses. Also, chromium(III) oxide is proposed as an effective catalyst for the conversion of (R)-(-)-laudanosine into (R)-(-)-glaucine.