Formal synthesis of the bisbenzylisoquinoline alkaloid berbamunine by asymmetric substitution of chiral organolithium compounds

by Gawley, Robert E.; Smith, Gregory A.

Asymmetric alkylation of enantiomeric tetrahydroisoquinolyl oxazolines was achieved with 96-97% diastereoselectivity. Removal of the oxazoline chiral auxiliary and further transformations provide a straightforward synthesis of the two synthetic intermediates that were previously synthesized by resolution, and which comprise a formal synthesis of berbamunine by Ullman coupling.

Journal
Arkivoc
Issue
5
Year
2011
Start Page
167
URL
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3192450/
ISBN/ISSN
1551-7012; 1551-7004