The akuammiline alkaloids are a structurally diverse family of indole natural products. Their complex structures and well-studied pharmacological properties render them attractive synthetic targets. Although more than 15 completed syntheses of akuammiline alkaloids have been reported in the past decade, those akuammilines that contain a methanoquinolizidine core have evaded total synthesis. This presentation will describe our enantioselective approach to these alkaloids, which culminates in the first total syntheses of (+)-strictamine and (–)-2(<i>S</i>)-cathafoline. In addition, the enantioselective total synthesis of (–)-aspidophylline A will be presented.

Enantioselective total synthesis of akuammiline alkaloids (+)-strictamine, (–)-2(<i>S</i>)-cathafoline, and (–)-aspidophylline A

253rd National Meeting (2017)

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Enantioselective total synthesis of akuammiline alkaloids (+)-strictamine, (–)-2(S)-cathafoline, and (–)-aspidophylline A