908005-82-3Relevant academic research and scientific papers
Asymmetric synthesis of enantioenriched (+)-elaeokanine A
Dieter, R. Karl,Chen, Ningyi
, p. 5674 - 5678 (2006)
The key transformation in the total synthesis of (+)-elaeokanine A was accomplished by asymmetric deprotonation of N-Boc pyrrolidine, followed by the reaction of the in situ generated enantioenriched stereogenic cuprate reagent with (E)-4-bromo-l-iodo-l-trimethylsilyl-l-butene with retention of configuration. N-Boc deprotection, followed by a one-pot olefin isomerization and intramolecular amine alkylation afforded a bicyclic vinyl bromide that was converted into (+)-elaeokanine A by sequential halogen metal exchange and reaction of the organolithium reagent with N-butanoylmorpholine.
