250261-54-2Relevant academic research and scientific papers
Stereoselective synthesis of (3R*,3aS*,7aS*)-3-aryloctahydroindol2-ones using radical cyclisation: A formal synthesis of (±)-pancracine
Ikeda, Masazumi,Hamada, Masahiro,Yamashita, Takashi,Matsui, Katsuaki,Sato, Tatsunori,Ishibashi, Hiroyuki
, p. 1949 - 1956 (2007/10/03)
The Bu3SnH- or (TMS)3SiH-mediated 5-emlo-trig radical cyclisation of the 7V-(cyclohex-l-enyl)acetamide 10 gives a mixture of the as-fused (3R*,3aS*,7aS*)- and trans-fused (3R*,3aS*,7aK*)-3-aryloctahydroindol-2-ones lia and lib, whereas the 5-cxo-trig radical cyclisation of the N-(cycIohex-2-enyl)acetamide 17 proceeds in a stereoselective manner to give only lia. The latter method has been applied to the synthesis of the 5,11-methanomorphanthridine derivative 30, a key intermediate for the synthesis of (±)-pancracine 1.
