Natural Product Synthesis & Chemical Biology

3. Total Syntheses of Lycopodium Alkaloids (+)-Fawcettimine, (+)-Fawcettidine, and...i

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Three fawcettimine‐ and serratinine‐type Lycopodium alkaloids are prepared from a common tetracyclic spirodiketone intermediate in concise total syntheses (see scheme). The intermediate was constructed by a remarkable biosynthesis‐inspired transannular NC bond formation to the spiro‐configured carbon center and a hydroxy‐directed pinacol coupling promoted by SmI.

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