54370-00-2Relevant articles and documents
Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization
Korch, Katerina M.,Watson, Donald A.
supporting information, p. 7285 - 7289 (2021/09/14)
The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds.
Copper-Catalyzed Aerobic Oxidative Cyclization Cascade to Construct Bridged Skeletons: Total Synthesis of (?)-Suaveoline
Tan, Qiuyuan,Yang, Zhao,Jiang, Dan,Cheng, Yuegang,Yang, Jiao,Xi, Song,Zhang, Min
supporting information, p. 6420 - 6424 (2019/04/13)
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.
Deconjugative alkylation/Heck reaction as a simple platform for dihydronaphthalene synthesis
Navaratne, Primali V.,Grenning, Alexander J.
supporting information, p. 69 - 75 (2016/12/27)
A simple platform for carbocycle synthesis by Knoevenagel adduct deconjugative alkylation/Heck reaction is described. Deconjugative alkylation of Knoevenagels adducts is two-fold synthetically enabling because C-C bond formation is (1) operationally simple due to the ease of Knoevenagel adduct carbanion generation and (2) results in alkene migration, which poises the substrate for cyclization. Furthermore, the gem-dinitrile moiety serves as a functional group for synthetic manipulation.
