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. 2017 Sep 15;19(18):4794-4797.
doi: 10.1021/acs.orglett.7b02210. Epub 2017 Sep 6.

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

Valentin Magné  1 , Charlotte Lorton  1 , Angela Marinetti  1 , Xavier Guinchard  1 , Arnaud Voituriez  1
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Short Enantioselective Total Synthesis of (-)-Rhazinilam Using a Gold(I)-Catalyzed Cyclization

Valentin Magné et al. Org Lett. .

Abstract

(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.

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