Catalytic Dearomatization Approach to Quinolizidine
Alkaloids: Five Step Total Synthesis
of (±)-Lasubine II

James, Michael
J.; Grant, Niall D.; O’Brien, Peter; J. K. Taylor, Richard; Unsworth, William P.

doi:10.1021/acs.orglett.6b03017.s001

ol6b03017_si_001.pdf (1.52 MB)

Catalytic Dearomatization Approach to Quinolizidine Alkaloids: Five Step Total Synthesis of (±)-Lasubine II

journal contribution

posted on 2016-11-30, 15:34 authored by Michael J. James, Niall D. Grant, Peter O’Brien, Richard J. K. Taylor, William P. Unsworth

A series of high-yielding silver(I)-catalyzed cyclization reactions of pyridine-, isoquinoline-, and pyrazine-ynones are described. The operationally simple and mild reaction conditions are a significant improvement over previously reported thermal cyclizations. The quinolizinone products were also used in a novel dearomatization strategy to prepare 0.53 g of the alkaloid lasubine II in five steps and 36% overall yield.