219143-70-1Relevant academic research and scientific papers
A concise synthesis of (-)-mesembrine
Dalko, Peter I.,Brun, Virginie,Langlois, Yves
, p. 8979 - 8982 (1998)
(-)-Mesembrine 11 was synthesized in 7 steps, in 19.4% overall yield and with ee>95%. The key step of the sequence is a stereoselective alkylation reaction of dianion derived from C2 symmetric imidazolines allowing efficient formation of quaternary benzylic center. Chiral auxiliaries derived from (S,S)-1,2-diamino-1,2-diphenylethane 1a and (S,S)-1,2-diaminocyclohexane 1b were compared. This synthesis provided unambiguous correlation of the newly formed stereocenter.
