Premium
Copper‐Catalyzed Aerobic Oxidative Cyclization Cascade to Construct Bridged Skeletons: Total Synthesis of (−)‐Suaveoline
Author(s) -
Tan Qiuyuan,
Yang Zhao,
Jiang Dan,
Cheng Yuegang,
Yang Jiao,
Xi Song,
Zhang Min
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902155
Subject(s) - iminium , total synthesis , chemistry , catalysis , ring (chemistry) , indole test , nonane , combinatorial chemistry , copper , organic chemistry
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 CuCl 2 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.