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Syntheses of rhazinilam. A comparative review of forty years of synthetic endeavors

2011, Kholod, Inga, Vallat, Olivier, Buciumas, Ana-maria, Neier, Reinhard

A review. 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 were 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 org. synthetic methods only a few synthetic strategies were applied to the total synthesis of rhazinilam. Astonishingly the no. of steps needed from com. starting materials has stayed similar over the almost 40 yr period since the first synthesis was reported in 1973. [on SciFinder(R)]