Total syntheses of Lycopodium alkaloids (+)-fawcettimine, (+)-fawcettidine, and (-)-8-deoxyserratinine.

A shared story: Three fawcettimine- and serratinine-type Lycopodium alkaloids are prepared from a common tetracyclic spirodiketone intermediate in concise total syntheses. The intermediate was constructed by a remarkable biosynthesis-inspired transannular N-C bond formation to the spiro-configured carbon center and a hydroxy-directed pinacol coupling promoted by SmI(2).