Formal synthesis of the bisbenzylisoquinoline alkaloid berbamunine by asymmetric substitution of chiral organolithium compounds
by Gawley, R. E.; Smith, G. 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
- Year
- 2011
- Start Page
- 167-179
- URL
- https://dx.doi.org/10.3998/ark.5550190.0012.514
- ISBN/ISSN
- 1551-7012; 1551-7004
- DOI
- 10.3998/ark.5550190.0012.514