Metal-catalyzed coupling reactions on an olefin template: the total synthesis of Bupleurynol

The naturally occurring polyacetylene Bupleurynol was synthesized in a convergent and stereospecific manner using a series of metal-mediated cross-coupling reactions. The synthesis demonstrates the utility of using a di-functional olefin template for the stereospecific synthesis of a disubstituted alkene product and its elaboration to a natural product target.