Ten-Step Total Synthesis of (-)-Andranginine

The total synthesis of the indole alkaloid (-)-an-dranginine has been achieved in 10 steps. Key reactions of the synthesis include a nucleophilic addition of acetylenyl anion to chiral N-sulfinyl imine, an intramolecular N-alkylation reaction to close the C ring, and a dienyne metathesis cascade reaction to construct the DE rings. Meanwhile, 16-epi-(-)-andranginine was also obtained with the developed strategy.

Automated summary

The total synthesis of the indole alkaloid (-)-an-dranginine has been achieved in 10 steps, involving key reactions including nucleophilic addition of acetylenyl anion, intramolecular N-alkylation reaction, and dienyne metathesis cascade reaction.