Cananodine is a member of the guaipyridine family of alkaloids and has significant activity against liver cancer. The skeleton of cananodine has stereocenters on the bicyclic core at C5 and C8. Previous work used the opening of an optically active epoxide to set the stereochemistry at C8.  We now present an Evans alkylation using a picolyl bromide derivative to set the C8 stereocenter.  This strategy allows for more efficient construction of the seven-membered ring of the target. The synthesis and characterization of a key intermediate will be presented.<br/>

Synthetic studies on cananodine: Setting the C8 stereocenter

255th National Meeting (2018)

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