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

Authors:
Robert E Gawley
Robert E Gawley
University of Arkansas
United States
Gregory A Smith
Gregory A Smith
Feinberg School of Medicine
United States

ARKIVOC 2011 Jan;2011(Pt 5):167-179

Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, U.S.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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3192450PMC
January 2011
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