84666-31-9Relevant academic research and scientific papers
Enantioselective Total Synthesis of Cerorubenic Acid-III via Type II [5+2] Cycloaddition Reaction
Liu, Xin,Liu, Junyang,Wu, Jianlei,Li, Chuang-Chuang
, p. 11125 - 11139 (2021/05/29)
The first enantioselective total synthesis of cerorubenic acid-III is described in detail. Different strategies and attempts, based on a type II [5+2] cycloaddition reaction, leading to the bicyclo[4.4.1] ring system with a strained bridgehead double bond, are depicted. Furthermore, sodium naphthalenide was found to be efficient in the chemoselective reduction of 8-oxabicyclo[3.2.1]octene, with three transformations completed in one operation. An unusual SN1 transannular cyclization reaction was applied to construct the synthetically challenging vinylcyclopropane moiety. This strategy enabled the total synthesis of cerorubenic acid-III in 19 steps.
Asymmetric Total Synthesis of Cerorubenic Acid-III
Liu, Xin,Liu, Junyang,Wu, Jianlei,Huang, Guocheng,Liang, Rong,Chung, Lung Wa,Li, Chuang-Chuang
supporting information, p. 2872 - 2877 (2019/02/19)
The first asymmetric total synthesis of the highly strained compound cerorubenic acid-III is reported. A type II intramolecular [5 + 2] cycloaddition allowed efficient and diastereoselective construction of the synthetically challenging bicyclo[4.4.1] ring system with a strained bridgehead (anti-Bredt) double bond in the final product. A unique transannular cyclization installed the vinylcyclopropane moiety with retention of the desired stereochemistry.
Regioselective hydrostannations catalyzed by molybdenum isonitrile complexes
Braune, Sascha,Kazmaier, Uli
, p. 26 - 29 (2007/10/03)
Hydrostannations using Mo(CO)3(CNtBu)3 give rise to α-stannylated alcohols and ethers in a highly regioselective fashion. The yields and selectivities obtained with this catalyst are significantly higher in comparison to t
Palladium(0) Catalyzed Hydrostannylation of Alkynes. Stereospecific Syn Addition of Tributyltin Hydride
Miyake, Hideyoshi,Yamamura, Kimiaki
, p. 981 - 984 (2007/10/02)
Tetrakis(triphenylphosphine)palladium(0) catalyzes the hydrostannylation of alkynes to give vinylstannanes in excellent yields.This reaction proceeds in syn manner.
