Rhodium(II)‐Catalyzed [4+3] Cyclization of Triazoles with Indole Derivatives and Its Application in the Total Synthesis of (±)‐Aurantioclavine. Issue 5 (13th April 2021)

• Record Type: Journal Article
• Authors: Duan, Shengguo; Xue, Bing; Meng, Hui; Ye, Zihang; Xu, Ze‐Feng; Li, Chuan‐Ying
• Is Part Of: Chinese journal of chemistry. Volume 39:Issue 5(2021)
• Page Start: 1145
• Page End: 1152
• Publication Date: 2021-04-13
• Subjects: Triazoles -- Rhodium -- Alkaloids -- Cyclization -- Aurantioclavine; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202000657
• Languages: English
• ISSNs: 1001-604X

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. Abstract : An efficient rhodium(II)‐catalyzed [4+3] cyclization reaction of 1‐sulfonyl‐1, 2‐3‐triazoles and indoles was developed. In addition, the total synthesis of (±)‐aurantioclavine was completed in four steps adopting this [4+3] cyclization as a key step.