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Review | Special issue | Vol 82, No. 2, 2010, pp.917-948
Published online, 2nd February, 2011
DOI: 10.3987/REV-10-SR(E)2
Synthesis of Rhazinilam: A Comparative Review of Forty Years of Synthetic Endeavors

Inga Kholod, Olivier Vallat, Ana-Maria Buciumas, and Reinhard Neier*

*Department of Chemistry, University of Neuchâtel, Avenue de Bellevaux 51, Case Postale 2, CH-2007 Neuchâtel, Switzerland


R-(-)-Rhazinilam is a relatively simple but unusual monopyrrolic product isolated from nature. It is probable that R-(-)-rhazinilam is an artifact of the isolation procedure. Seven total syntheses of rhazinilam have been described in the literature. The comparison of the published syntheses clearly demonstrates the sensitivity of the pyrrole ring contained in the rhazinilam structure. Despite the spectacular progress in organic synthetic methods only a few synthetic strategies have been applied to the total synthesis of rhazinilam. Astonishingly the number of steps needed from commercial starting materials has stayed similar over the almost 40 year period since the first synthesis has been reported in 1973.