Asymmetric formal synthesis of (−)-tetrazomine. Issue 8 (24th February 2021)

• Record Type: Journal Article
• Authors: Qi, Wei-Yi; Fang, Sheng-Long; Xu, Xue-Tao; Zhang, Kun; Shi, Bing-Feng
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 8(2021)
• Page Start: 1802
• Page End: 1807
• Publication Date: 2021-02-24
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00029b
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The asymmetric formal synthesis of (−)-tetrazomine, a structurally unique member of the tetrahydroisoquinoline alkaloids, is presented. Abstract : The asymmetric formal synthesis of (−)-tetrazomine is described. Key features of the synthesis include the efficient synthesis of (2 S, 3 R )-3-hydroxypipecolic acid via a Pd(ii )-catalyzed methylene C(sp 3 )–H acetoxylation, the stereoselective construction of the tetrahydroisoquinoline skeleton via Pd(ii )-catalyzed C(sp 3 )–H monoarylation and Pictet–Spengler reactions, and a Cu(i )-catalyzed exo -selective asymmetric [C + NC + CC] coupling reaction to build the chiral pyrrolidine scaffold.