Total Syntheses of Daphnezomine L-type and Secodaphniphylline-type <i>Daphniphyllum</i> Alkaloids via Late-Stage C–N Bond Activation

Abstract

Here, we report the first total syntheses of daphnezomine L-type alkaloids daphnezomine L methyl ester and calyciphylline K via late-stage C-N bond activation. The first synthesis of secodaphniphylline-type alkaloid caldaphnidine D was also achieved via a similar strategy. Other key transformations employed in our synthesis were a facile vicinal diol olefination and an efficient radical cyclization cascade. Biological studies indicated two synthetic compounds possess promising neuroprotective activity.

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