Rhodium(<scp>II</scp>)‐Catalyzed [4+3] Cyclization of Triazoles with Indole Derivatives and Its Application in the Total Synthesis of (±)‐Aurantioclavine
Shengguo Duan, Bing Xue, Hui Meng, Zihang Ye, Ze‐Feng Xu, Chuan‐Ying Li
Abstract
Main observation and conclusion An efficient rhodium(II)‐catalyzed [4+3] cyclization reaction of 1‐sulfonyl‐1,2‐3‐triazoles and indoles was developed. Azepino[5,4,3‐ cd ]indoles, which are widely distributed in ergot alkaloids with various biological activities, could be obtained in good to excellent yields. In addition, the total synthesis of (±)‐aurantioclavine was completed in four steps from the known compound 1a adopting this [4+3] cyclization as a key step.
Topics & Concepts
ChemistryRhodiumIndole testCatalysisTotal synthesisCombinatorial chemistrySulfonylReaction conditionsOrganic chemistryAlkylCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions