Journal of the American Chemical Society, Vol.132, No.24, 8506-8512, 2010
Total Synthesis of Enantiopure Phalarine via a Stereospecific Pictet-Spengler Reaction: Traceless Transfer of Chirality from L-Tryptophan
An appropriately constructed 2-substituted derivative of L-tryptophan undergoes conversion to a prephalarine structure in a single step. The reaction occurs in a diastereoselective fashion, leading shortly thereafter to the naturally occurring version of the alkaloid phalarine.