853356-49-7Relevant academic research and scientific papers
Remote stereocontrol in the Nazarov reaction: A new approach to the core of roseophilin
Occhiato, Ernesto G.,Prandi, Cristina,Ferrali, Alessandro,Guarna, Antonio
, p. 4542 - 4545 (2007/10/03)
Three different procedures are compared to obtain properly substituted divinyl ketones in which one of the double bonds is embedded in a five-membered heterocyclic structure and therefore suitable to produce cyclopenta-fused pyrrole derivatives by the acid-catalyzed Nazarov reaction. These, on treatment with TFA, afforded 2,4-cis-disubstituted 2,3,4,5-tetrahydro-1H-cyclopenta[e] pyrrol-6-ones with high stereo-control. One of these Nazarov products was oxidized to the corresponding 4,5-dihydro-1H-cyclopenta[e]pyrrol-6-one derivative, thus obtaining an enantiopure key intermediate in the total synthesis of roseophilin.
