Chemistry of Heterocyclic Compounds

, Volume 50, Issue 10, pp 1367–1387 | Cite as

Harmicine, a Tetracyclic Tetrahydro-β-Carboline: From the First Synthetic Precedent to Isolation from Natural Sources to Target-Oriented Synthesis (Review)*

  • C. S. Lood
  • A. M. P. KoskinenEmail author

Harmicine, a chiral tetrahydro-β-carboline with a rare tetracyclic pyrrolidine framework, was isolated from the plant Kopsia griffithii in 1998. Before that, harmicine had already appeared frequently in the chemical literature as a starting material for natural product synthesis and it had been used as a model substrate in various methodology studies. Herein we review the relevant information available on this heterocyclic natural product before and after its isolation and classification as a natural product.


tetrahydro-β-carboline asymmetric synthesis Bischler–Napieralski reaction natural product Pictet–Spengler reaction 


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© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Aalto University School of Chemical TechnologyAaltoFinland

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