American Chemical Society
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

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journal contribution
posted 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.