880643-58-3Relevant academic research and scientific papers
First asymmetric enantioselective total synthesis of phenanthridine alkaloid, (S)-(+)-asiaticumine and its enantiomer
Nishiyama, Takashi,Takaiwa, Shuuya,Kotouge, Rika,Tani, Satomi,Yoshinaga, Rikako,Hamada, Erina,Endo, Mai,Sugino, Yuka,Hatae, Noriyuki,Hibino, Satoshi,Choshi, Tominari
supporting information, (2019/11/05)
In this study, the first asymmetric enantioselective total syntheses of (+)-asiaticumine A (2) and its enantiomer were accomplished through a seven-step sequence using the bond formation between the C4a and N5 positions of the phenanthridine framework bas
Rhodium-Catalyzed Enantioselective Intramolecular Hydroacylation of Trisubstituted Alkenes
Johnson, Kirsten F.,Schneider, Eugene A.,Schumacher, Brian P.,Ellern, Arkady,Scanlon, Joseph D.,Stanley, Levi M.
supporting information, p. 15619 - 15623 (2016/10/24)
We report the first examples of transition metal-catalyzed enantioselective alkene hydroacylations with 1,1,2-trisubstituted alkenes. DFT and mechanistic studies are consistent with a reaction pathway for these rhodium-catalyzed processes including intramolecular alkene hydroacylation and α-epimerization to generate highly enantioenriched, polycyclic architectures. This reaction sequence enables the hydroacylation of 2-(cyclohex-1-en-1-yl)benzaldehydes to form hexahydro-9H-fluoren-9-ones in moderate to high yields (68–91 %) with high enantioselectivities (up to 99 % ee) and diastereoselectivities (typically >20:1).
A highly efficient synthesis of trispheridine through a construction of tetrahydrophenanthridine based on a microwave-assisted thermal electrocyclic reaction of an aza 6π-electron system
Kumemura, Teppei,Choshi, Tominari,Yukawa, Junko,Hirose, Aya,Nobuhiro, Junko,Hibino, Satoshi
, p. 87 - 90 (2007/10/03)
A highly efficient synthesis of a phenanthridine alkaloid, trispheridine (1) has been achieved in a 74% overall yield in a four-step sequence. The key step is the construction of a tetrahydrophenanthridine based on a microwave-assisted thermal electrocycl
