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