The akuammiline alkaloids are a family of natural products that have attracted significant synthetic interest in recent years due to their polycyclic architecture and biological activity. However, no total synthesis has yet been completed of any of the originally isolated alkaloids, such as akuammiline (1), akuammine (2), pseudoakummigine (3), and strictamine (4). These compounds remain a significant synthetic challenge due to their cage-like methanoquinolizidine cores. This presentation describes a cascade cyclization from an O-TMS hemiaminal ether precursor (5) that provides access to an indoline intermediate (6) containing some of the currently inaccesible structural motifs of the unsynthesized akuammiline alkaloids. This intermediate has been advanced to lactam (7), an intermediate that contains the full methanoquinolizidine carbocyclic framework. This presentation will also include a progress report on our application of these results toward the total synthesis of strictamine.

Progress toward the synthesis of the akuammiline alkaloid strictamine

251st National Meeting (2016)

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