Details

Autor(en) / Beteiligte

• Tan, Qiuyuan
• Yang, Zhao
• Jiang, Dan
• Cheng, Yuegang
• Yang, Jiao
• Xi, Song
• Zhang, Min

Titel

Copper‐Catalyzed Aerobic Oxidative Cyclization Cascade to Construct Bridged Skeletons: Total Synthesis of (−)‐Suaveoline

Ist Teil von

• Angewandte Chemie International Edition, 2019-05, Vol.58 (19), p.6420-6424

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Based on the discovery of copper‐catalyzed cyclopropanol ring‐opening addition to iminium ions, an unprecedented catalytic aerobic C−H oxidation/cyclopropanol cyclization cascade using CuCl2 as the multifunctional catalyst and air as the oxidant was developed to construct the azabicyclo[3.3.1]nonane skeleton, which is widespread in natural products and medicines. Using this method, concise asymmetric total synthesis of the indole alkaloid (−)‐suaveoline was achieved. This study not only provides an efficient, low‐cost, and environmentally benign method for constructing such bridged frameworks, but also enriches the realm of cyclopropanol chemistry and C−H functionalization. Walking on air: A new catalytic aerobic C−H oxidation/cyclopropanol ring‐opening cyclization cascade using CuCl2 as a multifunctional catalyst and air as the oxidant was developed to construct bridged azabicyclo[3.3.1]nonane frameworks. By using this reaction as the key step, a concise asymmetric total synthesis of the indole alkaloid (−)‐suaveoline was achieved.