Asymmetric Synthesis of (+)-Vellosimine Enabled by a Sequential Nucleophilic Addition/Cyclization Process

Herein, we achieved the asymmetric synthesis of (+)-vellosimine in 13 steps (longest linear sequences, LLS). This synthesis featured a sequential nucleophilic addition/cyclization process, which provided an efficient protocol for synthesizing a range of indole fused azabicyclo[3.3.1]nonane. Additionally, a SmI2-mediated reductive cyclization of ketone with an attached alpha,beta-unsaturated ester for constructing the strained quinuclidine moiety was also highlighted.

Automated summary

In this study, the asymmetric synthesis of (+)-vellosimine was achieved in 13 steps (longest linear sequences, LLS). The synthesis featured a sequential nucleophilic addition/cyclization process and highlighted the reductive cyclization of a ketone with an attached alpha,beta-unsaturated ester for constructing the strained quinuclidine moiety.