936649-35-3Relevant academic research and scientific papers
Structure elucidation and enantioselective total synthesis of the potent HMG-CoA reductase inhibitor FR901512 via catalytic asymmetric Nozaki-Hiyama reactions
Inoue, Masahiro,Nakada, Masahisa
, p. 4164 - 4165 (2007)
The structure elucidation and enantioselective total synthesis of the potent HMG-CoA reductase inhibitor FR901512 were accomplished. FR901512 was prepared in 15 steps from the commercially available 2-bromo-4-methylbenzaldehyde via FR901516 in 16.3% overa
AgOTf-catalyzed sequential synthesis of 4-isoquinolones: Via oxidative ring opening of aziridines and aza-Michael addition
Xing, Siyang,Cui, Hong,Gu, Nan,Li, Ying,Wang, Kui,Tian, Dawei,Qin, Jiajing,Liu, Qiaoyang
supporting information, p. 8308 - 8312 (2017/10/23)
An efficient AgOTf-catalyzed sequential reaction involving the oxidative ring-opening of aziridines by DMSO and aza-Michael addition has been developed. A series of 2,3-dihydro-4(1H)-isoquinolones were afforded in moderate to good yields by the formation of one new CO bond and one new C-N bond. The features of this sequential reaction include high bonding efficiency, use of a catalytic amount of catalysts, a broad substrate scope and mild conditions. This methodology provides a good choice for constructing the libraries of 2,3-dihydro-4(1H)-isoquinolones.
Palladium-Catalyzed Ring-Forming Aminoalkenylation of Alkenes with Aldehydes Initiated by Intramolecular Aminopalladation
Hu, Yue,Xie, Yinjun,Shen, Zhiqiang,Huang, Hanmin
, p. 2473 - 2477 (2017/02/23)
A palladium-catalyzed aminopalladation reaction followed by nucleophilic addition with aldehydes and dehydration is described. This direct and operationally simple procedure provides a rapid and reliable approach to a wide range of functionalized tetrahydroisoquinolines with high selectivity. Mechanistic studies disclosed that the nucleophilic addition, performed via a highly ordered transition-state, is the turnover-limiting step in which the inherent β-hydride elimination of the key Csp3?Pd species was controlled by the confined conformation and the nucleophilicity of the Csp3?Pd bond was enhanced by the strong electron-donating effect of the nitrogen atom.
Direct intramolecular conjugate addition of simple alkenes to α,β-unsaturated carbonyls catalyzed by Cu(OTf)2
Qin, Yan,Lv, Jian,Luo, Sanzhong,Cheng, Jin-Pei
supporting information, p. 5032 - 5035 (2014/12/11)
An unprecedented intramolecular conjugate addition of simple alkenes to α,β-unsaturated carbonyl compounds has been developed. A simple Lewis acid such as Cu(OTf)2 was found to effectively catalyze the reaction, and six- and five-membered cycli
Structure elucidation and enantioselective total synthesis of the HMG-CoA reductase inhibitors FR901512 and FR901516
Inoue, Masahiro,Nakada, Masahisa
experimental part, p. 3694 - 3707 (2010/03/30)
The enantioselective total synthesis of the potent HMGCoA reductase inhibitors FR901512 (1) and FR901516 (2) is reviewed. FR901512 was prepared in 15 steps from commercially available compound via 2 in 16.3% overall yield (89% average yield). This study validated the applicability and reliability of the catalytic asymmetric Nozaki-Hiyama reactions that were developed by us. These reactions enabled the concise, efficient, and protecting-group-free enantioselective total syntheses of these new statins.
