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

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

(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 forma...

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Veröffentlicht in:Organic letters 2017-09, Vol.19 (18), p.4794-4797
Hauptverfasser: Magné, Valentin, Lorton, Charlotte, Marinetti, Angela, Guinchard, Xavier, Voituriez, Arnaud
Format: Artikel
Sprache:eng
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Zusammenfassung:(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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02210