Oxazoles in Organic Chemistry. 2. Application to the Synthesis of Benzylisoquinoline Alkaloids

Article abstract of DOI:10.1021/jo01300a070

A conceptually new route to the benzylisoquinoline alkaloids has been devised.The reaction of 2-lithiooxazoles with aromatic aldehydes to generate the thermodynamically favored 2-substituted oxazoles constitutes the key step in this process.A single-pot two carbon-carbon bond-joining reaction leading to an oxazoline suitable for further transformation to a phenethylamide is also described.