Modular Total Synthesis of the 5/5-Spirocyclic Spiroindimicins

Total syntheses of the 5/5-spirocyclic indoline alkaloids (+/-)-spiroindimicins B, C, D, E, F, and G have been achieved via a modular approach. Our route features direct coupling of halogenated pyrrolemetal and isatin partners, Suzuki coupling to append the indole unit, Lewis acid-mediated spirocyclization, and divergent functionalization to give various family members. These syntheses are concise (six or seven steps from commercial materials) and highly amenable to analogue synthesis.

Automated summary

Total syntheses of the 5/5-spirocyclic indoline alkaloids have been achieved via a modular approach, which are concise and highly amenable to analogue synthesis.