4.8 Article

Total Synthesis of Enantiopure Phalarine via a Stereospecific Pictet-Spengler Reaction: Traceless Transfer of Chirality from L-Tryptophan

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 24, Pages 8506-8512

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja1030968

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Funding

  1. National Institutes of Health [HL25848]
  2. National Science Foundation [CHE-0619638]

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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.

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