The akuammiline alkaloids are a structurally diverse family of monoterpenoid indole natural products. Their complex structures, coupled with their well-studied pharmacological properties, have made them attractive synthetic targets. Despite these seminal studies, one structural class of the akuammiline alkaloids has remained inaccessible, namely, compounds that possess a methanoquinolizidine core. This presentation will describe a robust, unified, and asymmetric approach to access the methanoquinolizidine-containing akuammilines strictamine and 2(<i>S</i>)-cathafoline. In addition, the first enantioselective total synthesis of aspidophylline A will be described.

Total syntheses of the akuammiline alkaloids (+)-strictamine, (-)-2(<i>S</i>)-cathafoline, and (-)-aspidophylline A

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Total syntheses of the akuammiline alkaloids (+)-strictamine, (-)-2(S)-cathafoline, and (-)-aspidophylline A