ja1030968_si_001.pdf (4.64 MB)
Total Synthesis of Enantiopure Phalarine via a Stereospecific Pictet−Spengler Reaction: Traceless Transfer of Chirality from l-Tryptophan
journal contributionposted on 2010-06-23, 00:00 authored by John D. Trzupek, Dongjoo Lee, Brendan M. Crowley, Vasilios M. Marathias, Samuel J. Danishefsky
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.