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Short Enantioselective Total Synthesis of (−)-Rhazinilam Using a Gold(I)-Catalyzed Cyclization

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journal contribution
posted on 06.09.2017, 14:18 by Valentin Magné, Charlotte Lorton, Angela Marinetti, Xavier Guinchard, Arnaud Voituriez
(R)-(−)-Rhazinilam has been synthesized in nine steps and 20% overall yield. The key steps involve two metal-catalyzed processes: the enantioselective gold­(I)-catalyzed cycloisomerization of an allene-functionalized pyrrole and the palladium-catalyzed hydrocarboxylation of a vinyl moiety with formate as a CO surrogate. This novel strategy represents the shortest and highest yielding enantioselective total synthesis of (−)-rhazinilam.